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[ CAS No. 161957-56-8 ] {[proInfo.proName]}

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Chemical Structure| 161957-56-8

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Quality Control of [ 161957-56-8 ]

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Product Details of [ 161957-56-8 ]

CAS No. :	161957-56-8	MDL No. :	MFCD00665763
Formula :	C₇H₄BrFO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	UVKURTLVTLRSSM-UHFFFAOYSA-N
M.W :	219.01	Pubchem ID :	2736313
Synonyms :

Safety of [ 161957-56-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 161957-56-8 ]

* 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 [ 161957-56-8 ]
Downstream synthetic route of [ 161957-56-8 ]

[ 161957-56-8 ] Synthesis Path-Upstream 1~2

1
[ 161957-56-8 ]
[ 161957-61-5 ]

Reference： [1] Patent: US2008/76771, 2008, A1,

2
[ 161957-56-8 ]
[ 1195768-19-4 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 3, p. 358 - 362

[ 161957-56-8 ] Synthesis Path-Downstream 1~4

1
[ 161957-56-8 ]
[ 149-73-5 ]
[ 206551-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In methanol;	EXAMPLE 120 3-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-2-fluoro-benzonitrile A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 mL) under nitrogen was treated with trimethylorthoformate (0.22 mL, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. the organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H-NMR (CDCl3) delta7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz), 3.94 (s, 3H): MS (EI) 232 (M+).
	With toluene-4-sulfonic acid; In methanol;	EXAMPLE 68 2-fluoro-3-(1',2'-Dihydro-2'-oxospiro[cyclohexane-1,3'-[3H]indol-5'-yl)benzaldehyde oxime A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 ml) under nitrogen was treated with trimethylorthoformate (0.22 ml, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. The organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H NMR (CDCl3) delta7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz) and 3.94 (s, 3H): MS (EI) 232 (M+).
	With toluene-4-sulfonic acid; In methanol;	EXAMPLE 120 3-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-2fluoro-benzonitrile A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 mL) under nitrogen was treated with trimethylorthoformate (0.22 mL, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. the organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H-NMR (CDCl3) delta7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz), 3.94 (s, 3H): MS (EI) 232 (M+).

With toluene-4-sulfonic acid; In methanol;

EXAMPLE 68 2-Fluoro-3-(1',2'-dihydro-2'-oxospiro[cyclohexane-1,3'-[3H]indol]-5-yl) A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol 5 ml) under nitrogen was treated with trimethylorthoformate (0.22 ml, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. The organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H NMR (CDCl3) delta 7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz) and 3.94 (s, 3H): MS (EI) 232 (M+).

Reference： [1]Patent: US2002/49204,2002,A1
[2]Patent: US6391907,2002,B1
[3]Patent: US6444668,2002,B1
[4]Patent: US6462032,2002,B1

2
[ 67-56-1 ]
[ 161957-56-8 ]
[ 206551-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; for 1h;Inert atmosphere; Reflux;	To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoiotac acid (10 4 g, 10 47 5 mmol), MeOH (100 mL, 2472 mmol) and sulfuric acid (6 mL, 113 mmol) The reaction mixture was refluxed for 1 hr After cooling to rt, the MeOH was removed under reduced pressure and the acidic residue was poured into cold water and EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc The organic layers were combined, washed with brine, dried over sodium sulfate and 15 concentrated under reduced pressure to afford 10 02 g of methyl 3-bromo-2- fluorobenzoate 1H-NMR (400 MHz, DMSO-ds) delta 7 95 (ddd, J = 8 1 , 6 4, and 1 7 Hz, 1 H), 7 82 - 7 87 (m, 1 H), 7 26 (t, J =7 9 Hz, 1 H), and 3 86 (s, 3 H)
	With sulfuric acid; for 1h;Inert atmosphere; Reflux;	To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (10.4 g, 47.5 mmol), MeOH (100 mL, 2472 mmol) and sulfuric acid (6 mL, 1 13 mmol). The reaction mixture was refluxed for 1 hr. After cooling to rt, the MeOH was removed under reduced pressure and the acidic residue was poured into cold water and EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed with brine, dried over NaSO and concentrated under reduced pressure to afford methyl 3-bromo-2-fluorobenzoate. 10.02 g. 1H-NMR (400 MHz, DMSO-de) delta 7.95 (ddd, J = 8.1 , 6.4, and 1 .7 Hz, 1 H), 7.82 - 7.87 (m, 1 H), 7.26 (t, J =7.9 Hz, 1 H), and 3.86 (s, 3 H).
	With sulfuric acid; at 20℃; for 18h;	3-Bromo-2-fluorobenzoic acid was transformed to intermediate 4 using the same procedure reported in example intermediate 2 to afford the corresponding amine as pale yellow oil.

With sulfuric acid; for 1h;Reflux;

Intermediate 15: N-{3-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Methyl 3-bromo-2-fluorobenzoate; To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (10.4 g, 47.5 mmol), MeOH (100 mL, 2472 mmol) and sulfuric acid (6 mL, 113 mmol). The reaction mixture was refluxed for 1 hr. After cooling to rt, the MeOH was removed under reduced pressure and the acidic residue was poured into cold water and EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed with brine, dried over NaSO4 and concentrated under reduced pressure to afford 10.02 g of methyl 3-bromo-2-fluorobenzoate. 1H-NMR (400 MHz, DMSO-d6) delta 7.95 (ddd, J=8.1, 6.4, and 1.7 Hz, 1H), 7.82-7.87 (m, 1H), 7.26 (t, J=7.9 Hz, 1H), and 3.86 (s, 3H).

Reference： [1]Patent: WO2010/104899,2010,A1 .Location in patent: Page/Page column 162
[2]Patent: WO2011/59610,2011,A1 .Location in patent: Page/Page column 86
[3]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362
[4]Patent: US9126993,2015,B2 .Location in patent: Page/Page column 51
[5]Patent: US2009/298815,2009,A1 .Location in patent: Page/Page column 52-53

3
[ 161957-56-8 ]
[ 74-88-4 ]
[ 206551-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 50℃; for 24h;	To a solution of 3-bromo-2-fluorobenzoic acid (10 g, 0.045 mol) in N,N-dimethylformamide (50 mL) was added iodomethane (5 mL) dropwise. The reaction was heated to 50° C. for 24 hours. After the reaction was cooled and diluted with water (500 mL), ethyl acetate (200 mL) was added. The organic phase was separated, dried over MgSO4, filtered, and concentrated to provide the title compound

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4502 - 4505
[2]Patent: US2012/220572,2012,A1 .Location in patent: Page/Page column 85
[3]Organic Letters,2017,vol. 19,p. 1112 - 1115

4
[ 206551-41-9 ]
[ 161957-56-8 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; lithium hydroxide; In tetrahydrofuran; at 25 - 40℃; for 1.5h;Inert atmosphere;	Synthesis of (3a) To a solution of <strong>[206551-41-9]methyl 3-bromo-2-fluorobenzoate</strong> (4.78 g, 20.51 mmol) in THF (20 mL) and MeOH (10 mL) was added LiOH (1.47 g, 61.54 mmol) at 25 C. under N2. The mixture was stirred at 40 C. for 1.5 hrs. TLC indicated 3-bromo-2-fluorobenzoate was consumed completely and one new spot formed. The reaction was poured into water (30 mL), then the pH of the mixture was adjusted to 5-6 with 1 M HCl solution. The reaction mixture was then extracted with ethyl acetate (20 mL*4). the combined organic layers were combined and washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give 3-bromo-2-fluorobenzoic acid (3a) which was used directly in the next step without further purification. 1H NMR (400 MHz, MeOD) delta 7.90 (ddd, J=1.7, 6.5, 7.9 Hz, 1H), 7.83 (ddd, J=1.7, 6.3, 8.0 Hz, 1H), 7.19 (dt, J=0.9, 7.9 Hz, 1H), 3.31 (td, J=1.6, 3.3 Hz, 2H).

Reference： [1]Patent: US2019/315767,2019,A1 .Location in patent: Paragraph 0399; 0401

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Technical Information

? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hunsdiecker-Borodin Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Passerini Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Reactions of Dihalides ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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