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[ CAS No. 689291-89-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 689291-89-2
Chemical Structure| 689291-89-2
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Quality Control of [ 689291-89-2 ]

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Product Details of [ 689291-89-2 ]

CAS No. :689291-89-2 MDL No. :MFCD07779026
Formula : C7H4BrIO Boiling Point : No data available
Linear Structure Formula :- InChI Key :MOELYMOGQIDKNW-UHFFFAOYSA-N
M.W : 310.92 Pubchem ID :21973861
Synonyms :

Calculated chemistry of [ 689291-89-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.25
TPSA : 17.07 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 3.08
Log Po/w (SILICOS-IT) : 3.63
Consensus Log Po/w : 2.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.87
Solubility : 0.0424 mg/ml ; 0.000136 mol/l
Class : Soluble
Log S (Ali) : -2.74
Solubility : 0.562 mg/ml ; 0.00181 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.13
Solubility : 0.0229 mg/ml ; 0.0000738 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.92

Safety of [ 689291-89-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P273-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335-H413 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 689291-89-2 ]

* 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.

  • Downstream synthetic route of [ 689291-89-2 ]

[ 689291-89-2 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 689291-89-2 ]
  • [ 75-64-9 ]
  • [ 689291-90-5 ]
YieldReaction ConditionsOperation in experiment
100% In tetrahydrofuran; at 20℃; for 96h;Inert atmosphere; Intermediate 21; N-[(l￡)-(5-bromo-2-iodophenyI)methylidene]-2-methyl-2- ropanamine; To a solution of 2-1, 4-Br benzaldehyde (2.0 g, 6.4 mmol) in anhydrous THF (10 mL) was added tert-butylamine (2.0 mL, 19.3 mmol) and the reaction stirred at room temperature under a nitrogen atmosphere for 4 days. The reaction was concentrated in vacuo and partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the desired compound as a pale yellow solid in quantitative yield.
In tetrahydrofuran; at 20℃; for 40h; The product from Example 62C (2.28 g, 7.3 mmol) in THF (10 ML) was treated with t-butylamine (1.61 g, 22.0 mmol) and stirred under nitrogen at room temperature for 40 hours.The mixture was concentrated under reduced pressure and the residue was dissolved in 30 ML of methylene chloride.The methylene chloride was washed with 10 ML water and concentrated to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 8.29 (s, 1H), 8.05 (d, J=4 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.19 (dd, J=4, 8 Hz, 1H), 1.34 (s, 9H). MS (DCl/NH3) 366 [M+H]+.
In tetrahydrofuran; at 20℃; for 40h; The product from Example 15C (2.28 g, 7.3 mmol) in THF (10 mL) was treated with t-butylamine (1.61 g, 22.0 mmol) and stirred under nitrogen at room temperature for 40 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in 30 mL of methylene chloride. The methylene chloride was washed with 10 mL water and concentrated to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 8.29 (s, 1H), 8.05 (d, J=4 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.19 (dd, J=4, 8 Hz, 1H), 1.34 (s, 9H). MS (DCl/NH3) 366 [M+H]+.
In tetrahydrofuran; at 20℃; for 40h; Example 15D N-[(1E)-(5-Bromo-2-iodophenyl)methylene]-N-(tert-butyl)amine The product from Example 15C (2.28 g, 7.3 mmol) in THF (10 mL) was treated with t-butylamine (1.61 g, 22.0 mmol) and stirred under nitrogen at room temperature for 40 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in 30 mL of methylene chloride. The methylene chloride was washed with 10 mL water and concentrated to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 8.29 (s, 1H), 8.05 (d, J=4 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.19 (dd, J=4, 8 Hz, 1H), 1.34 (s, 9H). MS (DCl/NH3) 366 [M+H]+.
In tetrahydrofuran; at 20℃; for 40h;Inert atmosphere; To a stirred solution of <strong>[689291-89-2]5-bromo-2-iodobenzaldehyde</strong> (4.2 g, 13.5 mmol, 1 .0 equiv) in THF (20 ml_) was added t-butyl amine (4.26 ml_, 40.6 mmol, 3.0 equiv) at room temperature, under nitrogen atmosphere. The reaction mixture was stirred for 40 h at room temperature and evaporated under vacuum to obtain a residue. The residue was dissolved in DCM (100 ml_) washed with H20 (50 ml_), dried over sodium sulphate and evaporated to obtain (￡)-/V-(5-bromo-2-iodobenzylidene)-2-methylpropan-2-amine (3.0 g, crude) as a yellow oily compound. 1H NMR (400 MHz, CDCI3) δ ppm 1 .32 (s, 9H), 7.20 (dd, J=2.8, 8.4 Hz, 1 H), 7.68 (d, J=8.4 Hz, 1 H), 8.07 (d, J=2.4 Hz, 1 H), 8.31 (s, 1 H).

  • 2
  • [ 199786-58-8 ]
  • [ 689291-89-2 ]
YieldReaction ConditionsOperation in experiment
98% With dipyridinium dichromate; In dichloromethane; at 20℃; for 4h;Inert atmosphere; To a stirred solution of PDC (11.0 g, 0.0288 mol) in CH2Cl2 (60 mL) was added a solution of 11 (4.50 g, 0.0144 mol) in CH2Cl2 (20 mL). The mixed content was stirred for 4 h at rt. The solvent was then removed under vacuum to give the crude product of 12, which was purified by silica flash column chromatography (hexanes/CH2Cl2, 7:3) to give compound 12 (4.40 g, 0.0142 mol, 98%) as a white solid.
93% With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 - -10℃; for 1.25h;Inert atmosphere; A solution of oxalyl chloride (1 .99 mL, 23.04 mmol, 1 .6 equiv) in DCM (25 mL) was cooled to -70C and DMSO (2.44 mL, 34.5 mmol, 2.4 equiv) in DCM (25 mL) was added at -65C to -70C. The reaction mixture stirred for 10 minutes under nitrogen atmosphere at - 70C and then (5-bromo-2-iodophenyl)methanol (4.55 g, 14.4 mmol, 1 .0 equiv) in DCM (100 mL) was added. The reaction mixture was stirred at -65C for 15 minutes and triethylamine (10 mL, 72 mmol, 5.0 equiv) was added. The reaction mixture was allowed to warm to -10C and stir for 1 h. Water (40 mL) was added and the reaction mixture was allowed to warm to room temperature. The organic layer was separated and evaporated to obtain 5-bromo-2-iodobenzaldehyde (4.2 g, 93 %) as white solid. 1H NMR (400 MHz.CDCb) δ ppm 7.45 (d, J=7.6 Hz, 1 H), 7.81 (d, J=1 1 .6 Hz, 1 H), 7.98 (d, J=1 .6 Hz, 1 H), 9.97 (s, 1 H).
A solution of oxalyl chloride (1.53 g, 0.012 mol) in CH2Cl2 (15 ML) was cooled to -70 C., and DMSO (1.41 g, 0.018 mol) in CH2Ck (15 ML) was added at -65 to -70 C. The mixture was stirred under nitrogen for 10 minutes at -70 C. and then treated with the product from Example 62B (2.35 g, 7.5 mmol) in 60 ML CH2Cl2.The slurry was stirred at -65 C. for 15 minutes and treated with triethylamine (3.8 g, 0.037 mol).The mixture was allowed to warm to -10 C. over 1 hour.The mixture was treated with 20 ML of water and allowed to warm to room temperature.The organic layer was separated and concentrated to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 9.97 (s, 1H), 7.97 (d, J=4 Hz, 1H), 7.79 (d, J=8 Hz, 1H), 7.40 (dd, J=4, 8 Hz, 1H). MS (DCl/NH3) [M+NH4]+ at 328.
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 - -10℃; for 1.25h; A solution of oxalyl chloride (1.53 g, 0.012 mol) in CH2Cl2 (15 mL) was cooled to -70 C., and DMSO (1.41 g, 0.018 mol) in CH2Cl2 (15 mL) was added at -65 to -70 C. The mixture was stirred under nitrogen for 10 minutes at -70 C. and then treated with the product from Example 15B (2.35 g, 7.5 mmol) in 60 mL CH2Cl2. The slurry was stirred at -65 C. for 15 minutes and treated with triethylamine (3.8 g, 0.037 mol). The mixture was allowed to warm to -10 C. over 1 hour. The mixture was treated with 20 mL of water and allowed to warm to room temperature. The organic layer was separated and concentrated to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 9.97 (s, 1H), 7.97 (d, J=4 Hz, 1H), 7.79 (d, J=8 Hz, 1H), 7.40 (dd, J=4, 8 Hz, 1H). MS (DCl/NH3) [M+NH4]+ at 328.
Example 15C 5-Bromo-2-iodobenzaldehyde A solution of oxalyl chloride (1.53 g, 0.012 mol) in CH2Cl2 (15 mL) was cooled to -70 C., and DMSO (1.41 g, 0.018 mol) in CH2Cl2 (15 mL) was added at -65 to -70 C. The mixture was stirred under nitrogen for 10 minutes at -70 C. and then treated with the product from Example 15B (2.35 g, 7.5 mmol) in 60 mL CH2Cl2. The slurry was stirred at -65 C. for 15 minutes and treated with triethylamine (3.8 g, 0.037 mol). The mixture was allowed to warm to -10 C. over 1 hour. The mixture was treated with 20 mL of water and allowed to warm to room temperature. The organic layer was separated and concentrated to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 9.97. (s, 1H), 7.97 (d, J=4 Hz, 1H), 7.79 (d, J=8 Hz, 1H), 7.40 (dd, J=4, 8 Hz, 1H). MS (DCl/NH3) [M+NH4]+ at 328.
With dipyridinium dichromate; In dichloromethane; at 20℃; for 4h; The compound was synthesized according to the published procedure. [Zhou, N.; Wang, L.; Thompson, D. W.; Zhao, Y. Org. Lett. 2008, 10 (14), 3001-3004] Compound L15 and pyridinium dichromate (7.2 g, 19.2 mmol, 2 eq.) were dissolved in dry dichloromethane (40 ml) and the mixture was stirred at room temperature for 4 hours. The mixture was filtered through celite, washed with diethyl ether and solvents were evaporated. The solid was adsorbed on silica gel in a mixture of cyclohexane/acetone and it was purified by flash column chromatography on silica gel (cyclohexane to 20% ethyl acetate modified with 10% methanol (v/vi)), yielded 2.3 g (77%) of the title compound as a white solid (85% NMR purity). 1H NMR (401 MHz, Chloroform-d) δ 9.99 (s, 1H), 7.99 (d, J= 2.5 Hz, 1H), 7.81 (d, J= 8.4 Hz, 1H), 7.41 (dd, J= 8.4, 2.5 Hz, 1H). 13C NMR (101 MHz, Chloroform-d) δ 194.45, 141.95, 138.37, 136.47, 133.24, 123.63, 98.39. MS (CI-QMS) m/z: [M + H]+ calcd for C7H5BrIO, 310.9; found, 310.9.

  • 3
  • [ 689291-89-2 ]
  • [ 88284-48-4 ]
  • [ 3096-56-8 ]
  • 5
  • [ 689291-89-2 ]
  • [ 89343-06-6 ]
  • [ 1038395-11-7 ]
YieldReaction ConditionsOperation in experiment
94% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 24.0833h;Inert atmosphere; Compound 12 (1.62 g, 5.20 mmol), triisopropylsilylacetylene (1.15 mL, 0.950 g, 5.20 mmol), PdCl2(PPh3)2 (46 mg, 0.065 mmol), and CuI (25 mg, 0.13 mmol) were added to Et3N (20 mL). The solution was bubbled with N2 at rt for 5 min and then stirred at rt and under N2 protection for 24 h. After the reaction was completed as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 23, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 4:1) to yield compound 23 (1.78 g, 4.87 mmol, 94%) as a colorless oil. IR (KBr) 2944, 2891, 2866, 2736, 2156, 1695, 1582, 1469, 1383 cm-1; 1H NMR (CDCl3, 500 MHz) δ 10.53 (s, 1H), 8.05 (d, J=2.0 Hz, 1H), 7.67 (dd, J=8.5, 1.5 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 1.15 (s, 21H); 13C NMR (CDCl3, 125 MHz) δ 190.4, 137.5, 136.7, 135.4, 130.1, 125.9, 123.4, 101.1, 100.9, 18.8, 11.4; HRMS (CI) m/z calcd for C18H25BrOSi 364.0858, found 365.1071 [M+H]+.
  • 6
  • [ 75-77-4 ]
  • [ 689291-89-2 ]
  • [ 75-36-5 ]
  • 1-(2-iodo-5-bromo-phenyl)-3-trimethylsilyloxy-2-aza-1,3-butadiene [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 112b Preparation of intermediate 1-(2-iodo-5-bromo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene To dry tetrahydrofuran (120 mL) was added a solution of LiHMDS (42 mmol, 42 ml) in THF under argon at room temperature, followed by the addition of 5-bromo-2-iodo-benzaldehyde (13 g, 42 mmol). After the mixture was stirred at room temperature for 0.5 h, trimethylsilyl chloride (5.32 mL, 42 mmol) was added dropwise. Then the temperature of the mixture was lowered to 0 C. on a cooling ice bath. To this mixture was added triethylamine (7.6 mL, 54.4 mmol) in one portion, followed by the dropwise addition of a solution of acetyl chloride (3.9 mL, 54.4 mmol) in diethyl ether (200 mL). The cooling bath was removed, and the mixture was stirred at room temperature for 1 h. The mixture was quickly filtered on celite under nitrogen, and filtrate was concentrated under reduced pressure to give the title compound as a yellow gum and used for the next step without further purification.
  • 7
  • [ 121554-10-7 ]
  • [ 689291-89-2 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 112a Preparation of intermediate 5-bromo-2-iodo-benzaldehyde To a solution of 5-bromo-2-iodo-benzomitrile (1.54 g, 5 mmol) in DCM (15 mL) was added a solution of DIBALH (6 mL, 6 mmol) dropwise at 0 C. After the addition, the reaction mixture was warmed to r.t. and stirred for 2 h. Then the mixture was poured into 20 g of ice and 20 mL of 1N HCl, filtered and extracted by DCM (40 mL), washed with aqueous sodium bicarbonate, dried over MgSO4 and concentrated to give crude product (Yield: 1.2 g).
Step 1: 5-Bromo-2-iodo-benzaldehyde To <strong>[121554-10-7]5-bromo-2-iodobenzonitrile</strong> (7.4 g, 24.2 mmol) in THF (40 mL) at -78 C. was added diisobutylaluminium hydride (1M in hexanes; 24.2 mL, 24.2 mmol) over 5 minutes, and the reaction was allowed to warm to room temperature and monitored by analytical tlc. After stirring overnight at room temperature, starting material was still present, so the mixture was cooled to 0 C. and additional diisobutylaluminium hydride (1M in hexanes; 10.0 mL, 10.0 mmol) was added. After stirring for 2 hours at room temperature, no starting material was seen by analytical tlc, so the mixture was carefully quenched with freshly saturated aqueous Na2SO4 and diluted with EtOAc. The mixture was stirred vigorously for 1 hour and then filtered through Celite. The filtrate was concentrated, and the resulting oil solidified on standing. The solid was stirred vigorously in CH2Cl2 and 1N aqueous HCl, and the aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.
T o a s o l u t i o n o f <strong>[121554-10-7]5-bromo-2-iodobenzonitrile</strong> (5.0Og, 16 00mmoles) in anhydrous tetrahydrofuran (80ml) at -8O0C is added diisobutyl aluminium hydride (16.0ml, 16.0mmoles, 1 M solution in toluene) dropwise over 10 minutes. The reaction mixture is stirred at -8O0C for a 1 hour, then allowed to warm to ambient temperature and stir overnight. Additional diisobutyl aluminium hydride (16.0ml, 16.0mmoles, 1 M solution in toluene) is next added dropwise at room temperature, and the reaction mixture further stirred for 1hour. After careful quenching with 2M hydrochloric acid (cooling in ice bath), the crude product is extracted with ethyl acetate (x 2), then all organics are combined and dried over magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure then purified by flash column chromatography (isohexane to 10% ethyl acetate in isohexane eluant) to afford 5-bromo-2- iodobenzaldehyde (0.85g).
  • 8
  • [ 689291-89-2 ]
  • [ 75-04-7 ]
  • [ 1175525-90-2 ]
YieldReaction ConditionsOperation in experiment
Step 2: (5-Bromo-2-iodo-benzyl)-ethyl-amine To 5-bromo-2-iodo-benzaldehyde (5.0 g, 16.1 mmol) in MeOH (20 mL) was added ethylamine (2M in MeOH; 16 mL, 24.0 mmol), followed by acetic acid (1.0 mL, 17.8 mmol), and the mixture was stirred at room temperature for 30 minutes. Sodium cyanoborohydride (2.0 g, 31.8 mmol) was then added over 5 minutes, and the reaction was stirred at room temperature over the weekend. The mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound.
  • 9
  • [ 689291-89-2 ]
  • [ 64-17-5 ]
  • [ 1222168-93-5 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; for 18h;Reflux; Step 1: A mixture of <strong>[689291-89-2]5-bromo-2-iodobenzaldehyde</strong> (14.9) (1.0 g, 3.2 mmol) and PTSA (0.1 g) in ethanol was stirred under reflux for 18 hrs and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated NaHCC>3, dried over anhydrous Na2SC^ and concentrated to give 4-bromo-2-(diethoxymethyl)-l-iodobenzene (14.10) that was directly used in next reaction without further purification.
  • 10
  • [ 4414-88-4 ]
  • [ 689291-89-2 ]
  • [ 1219685-39-8 ]
  • 11
  • [ 689291-89-2 ]
  • [ 5455-94-7 ]
  • [ 1257065-29-4 ]
YieldReaction ConditionsOperation in experiment
To an ice-cold solution of 2,2,5, 5-tetramethyldihydrofuran-3-one (0.388g, 2.73mmoles) in anhydrous 1 ,2-dιmethoxyethane (5ml) is added sodium methoxide (0.177g, 3.27mmoles) in one portion. The reaction mixture is stirred for 5 minutes at this temperature, followed by the dropwise addition of 5-bromo-2-iodo-benzaldehyde (0.85Og, 2.73mmoles) as a solution in 1 ,2-dimethoxyethane (5ml). The reaction mixture is further stirred at O0C for 30 minutes, then at ambient temperature for a 1 hour. After partitioning between 1 M hydrochloric acid and dichloromethane, the organic phase is separated, and the aqueous phase is extracted again with additional dichloromethane. All organics are combined then concentrated in vacuo to afford 4-[1-(5-bromo-2-iodophenyl)methylιdene]-2,2,5,5-tetramethyldihydrofuran-3-one(1.18g) as a yellow gum.
  • 12
  • [ 689291-89-2 ]
  • [ 1038395-09-3 ]
  • 13
  • [ 689291-89-2 ]
  • [ 1038395-10-6 ]
  • 14
  • [ 689291-89-2 ]
  • C54H34 [ No CAS ]
  • 15
  • [ 689291-89-2 ]
  • [ 1038395-15-1 ]
  • 16
  • [ 689291-89-2 ]
  • C62H54N4 [ No CAS ]
  • 17
  • [ 689291-89-2 ]
  • [ 1263055-18-0 ]
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Technical Information

? Alkyl Halide Occurrence ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Kinetics of Alkyl Halides ? Knoevenagel Condensation ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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; ;