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Quality Control of [ 42872-74-2 ] Purity: 98% SDS Specification

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Product Details of [ 42872-74-2 ]

CAS No. :	42872-74-2
Formula :	C₈H₆BrN
M.W :	196.04
MDL No. :	MFCD06797818
InChI Key :	VXUMRYMTYKDWMO-UHFFFAOYSA-N
Pubchem ID :	14004840

Safety of [ 42872-74-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332
Precautionary Statements:	P280

Calculated chemistry of [ 42872-74-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	43.82
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	23.79 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.11
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.7
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.63
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.52
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.94
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.58

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.2
Solubility	0.124 mg/ml ; 0.00063 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.85
Solubility	0.275 mg/ml ; 0.0014 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.73
Solubility	0.0368 mg/ml ; 0.000188 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.58 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.89

Application In Synthesis [ 42872-74-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 42872-74-2 ]
Downstream synthetic route of [ 42872-74-2 ]

[ 42872-74-2 ] Synthesis Path-Upstream 1~2

1
[ 42872-74-2 ]
[ 89892-39-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 85℃; for 18 h; Inert atmosphere	To a stirred solution of 3-bromo-4-methyl-benzonitrile (2 g, 10.2014 mmol, 100 mass percent) in carbon tetrachloride (20 ml_, 100 mass percent) under argon, was added NBS (2.2 g., 12.2417 mmol, 99 mass percent) and benzoyl peroxide (0.123 g., 0.5101 mmol, 100 mass percent). The mixture was heated to 85°C for 18h. The reaction mass was diluted with water (50 ml) and extracted with ethyl acetate. Organics were washed again with water and brine, dried and evaporated to afford 3-bromo-4-(bromomethyl) benzonitrile (1.2 g, 4.4 mmol, 90 mass percent, 95percent Yield) as an off white solid solid. H NMR (400 MHz, chloroform-c) δ ppm 3.89 - 4.01 (m, 2 H) 6.61 - 6.77 (m, 1 H) 6.92 - 7.07 (m, 2 H) LCMS: RT 1.12-1.49 Min 274 [M+H] ⁺
52.5%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethaneInert atmosphere; Reflux	The compound 57 (804 mg, 4.04 mmol) was dissolved in carbon tetrachloride (8 mL), and then added with NBS (730 mg, 4.10 mmol) and benzoyl peroxide (7 mg, 0.0289 mmol). The resulting mixture was heated under the protection of nitrogen until reflux occurred, and was stirred overnight. The mixture was cooled to room temperature, filtered to remove insoluble substances and distilled under reduced pressure to remove the solvent, then dissolved in ethyl acetate (30 mL) and respectively washed with water (10 mL) and saturated saline solution (10 mL). After the solvent was removed by means of reduced pressure distillation, the resulting product was purified by using a silica column (200 to 300 mesh silica gel, ethyl acetate/petroleum ether=1/35 for elution) to obtain 3-bromo-4-cyanobenzyl bromide (58) (583 mg), with a yield of 52.5percent.

Reference： [1] Patent: WO2016/113303, 2016, A1, . Location in patent: Page/Page column 41
[2] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 829 - 835
[3] Journal of the American Chemical Society, 2009, vol. 131, # 39, p. 13908 - 13909
[4] Patent: EP2927219, 2015, A1, . Location in patent: Paragraph 0130; 0132
[5] Journal of Organic Chemistry, 1964, vol. 29, p. 2034 - 2036
[6] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 21, p. 3821 - 3825
[7] Patent: WO2010/85581, 2010, A1, . Location in patent: Page/Page column 71-72
[8] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 644 - 651
[9] Patent: WO2011/22337, 2011, A1, . Location in patent: Page/Page column 104

2
[ 42872-74-2 ]
[ 956218-04-5 ]

Reference： [1] Synlett, 2007, # 14, p. 2179 - 2184

[ 42872-74-2 ] Synthesis Path-Downstream 1~24

1
[ 42872-74-2 ]
[ 183723-09-3 ]

Yield	Reaction Conditions	Operation in experiment
	With Rhodococcus rhodochrous ATCC BAA 870 cobalt nitrile hydratase; In aq. buffer; at 30℃;pH 7.6;Enzymatic reaction;	General procedure: 1800 muL (90%) Tris buffer (50 mM, pH 7.6) and 200 muL(10%) of methanol or acetone. In a 2 mL Eppendorf, NHase (10 mg) was added followed by Trisbuffer. Nitrile substrate (10 mg dissolved in 200 muL methanol or acetone) was added to the 2 mLEppendorf tube. (If an amine group was present on the nitrile substrate a Tris buffer of pH 9 wasused). The reaction mixture was incubated at 30 C on an ESCO Provocell microplateshaker/incubator (Esco Technologies, Halfway House, South Africa) (199 rpm). The reaction wasallowed to proceed for 24 h, 48 h or 5 d, depending on conversion, as monitored by TLC analysis.Ethyl acetate and water were added to the reaction mixture, and after separation, the organic layerwas concentrated under reduced pressure, and the resulting mixture was then purified by silica gelcolumn chromatography eluting with 20% to 90% ethyl acetate/ hexane.

Reference： [1]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036
[2]Molecules,2020,vol. 25

2
[ 42872-74-2 ]
[ 89892-39-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 85℃; for 18h;Inert atmosphere;	To a stirred solution of <strong>[42872-74-2]3-bromo-4-methyl-benzonitrile</strong> (2 g, 10.2014 mmol, 100 mass%) in carbon tetrachloride (20 ml_, 100 mass%) under argon, was added NBS (2.2 g., 12.2417 mmol, 99 mass%) and benzoyl peroxide (0.123 g., 0.5101 mmol, 100 mass%). The mixture was heated to 85C for 18h. The reaction mass was diluted with water (50 ml) and extracted with ethyl acetate. Organics were washed again with water and brine, dried and evaporated to afford 3-bromo-4-(bromomethyl) benzonitrile (1.2 g, 4.4 mmol, 90 mass%, 95% Yield) as an off white solid solid. H NMR (400 MHz, chloroform-c) delta ppm 3.89 - 4.01 (m, 2 H) 6.61 - 6.77 (m, 1 H) 6.92 - 7.07 (m, 2 H) LCMS: RT 1.12-1.49 Min 274 [M+H] +
52.5%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Inert atmosphere; Reflux;	The compound 57 (804 mg, 4.04 mmol) was dissolved in carbon tetrachloride (8 mL), and then added with NBS (730 mg, 4.10 mmol) and benzoyl peroxide (7 mg, 0.0289 mmol). The resulting mixture was heated under the protection of nitrogen until reflux occurred, and was stirred overnight. The mixture was cooled to room temperature, filtered to remove insoluble substances and distilled under reduced pressure to remove the solvent, then dissolved in ethyl acetate (30 mL) and respectively washed with water (10 mL) and saturated saline solution (10 mL). After the solvent was removed by means of reduced pressure distillation, the resulting product was purified by using a silica column (200 to 300 mesh silica gel, ethyl acetate/petroleum ether=1/35 for elution) to obtain 3-bromo-4-cyanobenzyl bromide (58) (583 mg), with a yield of 52.5%.
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chloroform; at 40 - 50℃;Reflux;	5-C. 3-Bromo-4-(bromomethyl)benzonitrile; [00161] A solution of <strong>[42872-74-2]3-bromo-4-methylbenzonitrile</strong> (1 g, 5.10 mmol) in chloroform (20 mL) was heated to 40-50 0C and N-bromosuccinimide (0.953 g, 5.36 mmol) was added in one portion followed by AIBN (8.38 mg, 0.051 mmol). After 1.5 hr. additional AIBN (20mg) was added and the reaction was allowed to stir at 50 0C overnight. Additional AIBN (20mg) and N-bromosuccinimide (l.lg) were added, a reflux condenser was attached and the solution was heated to reflux. After several hours, additional AIBN (20mg) was added and the reaction was allowed to stir at reflux overnight. The reaction was quenched by the addition of water and sat. aq. sodium bicarbonate. The organic phase was separated, concentrated in vacuo and purified by flash column chromatography (12Og silica, eluting with 0%-20% Ethyl Acetate in hexanes) to afford 3-bromo-4-(bromomethyl)benzonitrile as a pale yellow solid (800 mg, 2.88 mmol). 1H NMR (500 MHz, MeOD) delta ppm 4.70 (s, 2H), 7.71 (d, J= 8.0 Hz, IH), 7.73 (d, J= 8.0 Hz, IH), 8.04 (s, IH).

	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 16h;Reflux; Inert atmosphere;	General procedure: To 2-bromo-3-methylbenzoic acid (21, 159 g, 739 mmol) in dichloromethane (1000 mL) was added triethylamine (TEA, 119.7 mL, 813 mmol, 1.1 equiv) followed by iso-butyl chloroformate (101.5 mL, 813 mmol, 1.1 equiv) in dichloromethane (DCM, 200 mL) at 0 C over 10 min. Concentrated ammonia water (323 mL) was then added at 0 C over 2 min. The reaction mixture was poured into water (200 mL), cooled to rt and filtered. The solid was washed with water (2 × 300 mL), 0.5 N HCl (2 × 150 mL) and dried to give the amide as a solid (120 g, yield 76%). To the solution of the amide obtained (50 g, 233.6 mmol) in DMF (300 mL) was added 2,4,6-trichloro-1,3,5-triazine (64.6 g, 350.4 mmol, 1.5 equiv) dropwise at 0 C and the reaction was stirred at rt overnight. To the reaction was added 600 mL of water and the reaction was stirred for 30 min. All insoluble was removed by filtration and the solid was triturated with ethyl acetate (EA, 3 × 100 mL) for 40 min and filtered. The filtrate was washed with saturated sodium carbonate (3 × 200 mL), saturated sodium chloride (200 mL) and dried over anhydrous sodium sulfate.The solvent was removed under reduced pressure to give 22 as a solid (42 g, yield 87.3%). To a solution of 22 (20 g, 102.2 mmol, 1 equiv) in CCl4 (200 mL) was added NBS (18.2 g, 102.0 mmol, 1.0 equiv), Bz2O2 (0.15 g, 0.6 mmol, 0.006 equiv). The reaction was refluxed overnight under N2, cooled and filtered. The filtrate was crystallized at 0 C to provide the brominated intermediate (15 g, yield 53.6%). To a solution of the brominated intermediate (90 g, 327.3 mmol) in DMF (760 ml) was added KOAc (38.6 g, 393.1 mmol, 1.2 equiv). The reaction mixture was stirred at 80 C for 1 h, cooled and water (1 L) was added. The mixture was extracted with EA (1 L). The organic layer was washed with 0.5 N HCl (3 ×200 mL), 2% NaHCO3 (200 mL) and dried over anhydrous sodium sulfate. The solvent was removed to give 23 as a yellow solid (77.3 g, yield 92.9%). 1H NMR of 23 (500 MHz, CDCl3): delta 2.16 (s, 3H), 5.21 (s, 2H), 7.43-7.46 (t, 1H,), 7.63 (m, 2H) ppm. To a solution of 23 (20 g, 78.8 mmol) in 1,4-dioxane (400 mL) was added bis(pinacolato)diboron (30 g, 118.1 mmol, 1.5 equiv) and KOAc (33.2 g, 338.1 mmol, 4.3 equiv). After being de-gassed and backfilled with nitrogen, Pd(dppf)Cl2 (3.2 g, 3.935 mmol, 0.05 equiv) was added. The reaction was refluxed overnight under nitrogen, cooled and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography eluted with petroleum ether (PE)/EA = 5:1 to give 24 as red oil (29 g, crude yield 100% with 80% purity). 1H NMR of 24 (500 MHz, DMSO-d6): delta 1.42 (s, 12H), 2.20 (s, 3H), 5.25 (s, 2H), 7.44-7.49 (t, 1H), 7.57-7.64 (m, 2H) ppm. To a solution of 24 (29 g) in MeOH (100 mL) was added a solution of NaOH in MeOH (7.0 g/130 mL, 175.8 mmol, 2.3 equiv) and the reaction was stirred for 2 h at rt. The reaction mixture was concentrated under vacuum and the residue was dissolved in THF (150 mL) and 2 N HCl (138 mL, 69 mmol, 0.9 equiv). The reaction was stirred at rt for 50 min, concentrated and filtered. The solid was washed with water (3 × 20 mL) and petroleum ether (3 × 20 mL) to provide 25 (7.6 g, yield 62%). 1H NMR of 25 (500 MHz, DMSO-d6): delta 5.05 (s, 2H), 7.63-7.68 (t, 1H), 7.73-7.81 (m, 2H) ppm. To Raney Ni (0.849 g, 14.5 mmol, 2.3 equiv) in formic acid (10 mL) and water (2 mL) was added 25 (1 g, 6.29 mmol) at rt. The reaction was stirred at 100 C for 1 h, cooled and then filtered. The solvent was removed to give a solid that was purified by silica gel column chromatography eluted with CH2Cl2 to give 26 as a solid (0.714 g, yield 70%). 1H NMR of 26 (500 MHz, CDCl3): delta 10.03 (s, 1H), 8.08 (s, 1H), 7.86 (t, 1H), 7.63-7.71 (m, 2H), 5.20 (s, 2H) ppm. To a mixture of HCOOH (116.2 g, 10.0 equiv) and TEA (102.2 g, 4.0 equiv) were added 26 (40.9 g, 252.5 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (43.7 g, 1.2 equiv). The resulting mixture was refluxed for 15 h and cooled to rt. Hydrochloric acid (2 N, 320 mL) was added into the mixture that was then extracted with ethyl acetate twice (2 × 250 mL). The combined organic layer was washed with 2 N HCl (160 mL) and rotary evaporated to give the crude product that was recrystallized from DMF and 2 N HCl (34:204 mL) providing compound 1 as a white solid (15.6 g, yield 30%). An additional recrystallization from DMF and 2 N HCl (16:96 mL) was performed to give high purity product (12.9 g).
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Reflux;	To a solution of <strong>[42872-74-2]3-bromo-4-methylbenzonitrile</strong> (276 g, 1.41 mol) in CCl4 (3.0 L) was added benzoyl peroxide (BPO, 3.0 g) and NBS (298.0 g, 1.65 mol). The mixture was stirred at refluxing temperature overnight. The mixture was cooled and diluted with DCM, washed with water and concentrated in vacuum to give 3-bromo- 4-(bromomethyl)benzonitrile (415 g) as a crude product which was used for next step directly without further purification.

Reference： [1]Patent: WO2016/113303,2016,A1 .Location in patent: Page/Page column 41
[2]Journal of the American Chemical Society,2017,vol. 139,p. 829 - 835
[3]Journal of the American Chemical Society,2009,vol. 131,p. 13908 - 13909
[4]Patent: EP2927219,2015,A1 .Location in patent: Paragraph 0130; 0132
[5]Organic Letters,2020,vol. 22,p. 1624 - 1627
[6]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036
[7]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3821 - 3825
[8]Patent: WO2010/85581,2010,A1 .Location in patent: Page/Page column 71-72
[9]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 644 - 651
[10]Patent: WO2011/22337,2011,A1 .Location in patent: Page/Page column 104

3
[ 42872-74-2 ]
[ 98-86-2 ]
α-(5-cyano-2-methylphenyl)acetophenone [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 645 - 647

4
[ 121-43-7 ]
[ 42872-74-2 ]
[ 867333-43-5 ]

Yield	Reaction Conditions	Operation in experiment
53%		Step 1 : Synthesis of 5-cyano-2-methylphenylboronic acid First, 9.5 g (50 mmol) of <strong>[42872-74-2]3-bromo-4-methylbenzonitrile</strong> was put into a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. Then, 250 mL of tetrahydrofuran (THF) was added, and the mixture was stirred at -78 C for 30 minutes. Into this mixed solution, 34 mL (55 mmol) of a 1.63M hexane solution of -butyllithium (-BuLi) was dropped, followed by stirring at -78 C for 1.5 hours. After that, 7.3 mL (65 mmol) of trimethyl borate was added to the mixture and this solution was stirred for 20 hours while the temperature was raised to room temperature. To this solution was added 100 mL of 1M hydrochloric acid and stirring was performed for 30 minutes. The obtained mixture was separated to an aqueous layer and an organic layer, and the aqueous layer was subjected to extraction with ethyl acetate. The organic layer and a solution of the extract were combined, and washed with saturated saline. Anhydrous magnesium sulfate was added to the obtained solution for drying. The obtained mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. This solid was washed with toluene and hexane, so that 4.3 g of a white solid was obtained in a yield of 53 %. The obtained white solid was identified as 5-cyano-2-methylphenylboronic acid by nuclear magnetic resonance ( MR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-10) below.

Reference： [1]Patent: WO2016/203350,2016,A1 .Location in patent: Paragraph 1195
[2]Journal of the American Chemical Society,2002,vol. 124,p. 9014 - 9015

5
[ 42872-74-2 ]
[ 956218-04-5 ]

Reference： [1]Synlett,2007,p. 2179 - 2184

6
[ 42872-74-2 ]
C₁₀H₇NO₂ [ No CAS ]

Reference： [1]Synlett,2007,p. 2179 - 2184

7
[ 42872-74-2 ]
[ 450839-99-3 ]