2-(2-bromo-3-methylphenyl)acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-3-methylbenzylcyanid (8.8 g, 42 mmol) was added to a mixture of conc sulfuric acid (50 ml) and water (60 ml) and was refluxed overnight. Water (150 ml) and diethyl ether were added and the organic layer was separated. To the organic layer was added a saturated sodium bicarbonate solution and the aqueous layer was separated. The aqueous layer was made acidic by additon of conc sulfuric acid. The acidic water solution was extracted with diethyl ether and the organic layer was washed with water, dried (Na2SO4) and evaporated under reduced pressure to give 6.5 g of the title compound. was refluxed overnight the organic layer was separated To the organic layer was added a saturated sodium bicarbonate solution the aqueous layer was separated The acidic water solution was extracted with diethyl ether the organic layer was washed with water dried (Na2SO4) evaporated under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-brom-3-methylbenzylbromide (25 g, 0.095 mol) and potassium cyanide (16 g, 0.25 mol) in dimethylformamide (100 ml) was stirred at 90° C. for 20 h. The solvent was evaporated under reduced pressure and to the residue were added toluene and water. The organic layer was separated washed with water, separated and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride as eluent gave 8.8 g (44%) of the title compound. The solvent was evaporated under reduced pressure and to the residue were added toluene and water The organic layer was separated washed with water separated evaporated under reduced pressure Purification of the residue by column chromatography on silica gel

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-brom-3-methylbenzylbromide (25 g, 0.095 mol) and potassium cyanide (16 g, 0.25 mol) in dimethylformamide (100 ml) was stirred at 90° C. for 20 h. The solvent was evaporated under reduced pressure and to the residue were added toluene and water. The organic layer was separated washed with water, separated and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride as eluent gave 8.8 g (44%) of the title compound. The solvent was evaporated under reduced pressure and to the residue were added toluene and water The organic layer was separated washed with water separated evaporated under reduced pressure Purification of the residue by column chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-bromo-3-methylphenyl)acetonitril (8.0 g, 0.038 mol) was added to a mixture of water (60 ml) and sulfuric acid (50 ml) and the mixture was refluxed overnight. After cooling to room temperature water (200 ml) was added and the mixture was extracted twice with methylene chloride. The methylene chloride extracts were combined, washed twice with water, dried and evaporated under reduced pressure to give 7.9 g (90.8%) of the title compound. the mixture was refluxed overnight was added the mixture was extracted twice with methylene chloride washed twice with water dried evaporated under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-1-(bromomethyl)-3-methylbenzene (15 g, 0.057 mmol) and potassium cyanide (9.6 g, 0. 148 mol) were added to dimethylformamide (75 ml) and stirred at 90° C. overnight. The solvent was evaporated under reduced pressure and the residue partitioned between water (150 ml) and methylene chloride. The aqueous layer was extracted twice with methylene chloride, the organic extracts was separated, washed twice with water and was evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:methylene chloride (3:7) as eluent gave 8.0 g (67%) of the title compound. The solvent was evaporated under reduced pressure the residue partitioned between water (150 ml) and methylene chloride The aqueous layer was extracted twice with methylene chloride the organic extracts was separated washed twice with water was evaporated under reduced pressure Purification of the residue by column chromatography on silica gel

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-1-(bromomethyl)-3-methylbenzene (15 g, 0.057 mmol) and potassium cyanide (9.6 g, 0. 148 mol) were added to dimethylformamide (75 ml) and stirred at 90° C. overnight. The solvent was evaporated under reduced pressure and the residue partitioned between water (150 ml) and methylene chloride. The aqueous layer was extracted twice with methylene chloride, the organic extracts was separated, washed twice with water and was evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:methylene chloride (3:7) as eluent gave 8.0 g (67%) of the title compound. The solvent was evaporated under reduced pressure the residue partitioned between water (150 ml) and methylene chloride The aqueous layer was extracted twice with methylene chloride the organic extracts was separated washed twice with water was evaporated under reduced pressure Purification of the residue by column chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-3-methylbenzylcyanid (8.8 g, 42 mmol) was added to a mixture of conc sulfuric acid (50 ml) and water (60 ml) and was refluxed overnight. Water (150 ml) and diethyl ether were added and the organic layer was separated. To the organic layer was added a saturated sodium bicarbonate solution and the aqueous layer was separated. The aqueous layer was made acidic by addition of conc sulfuric acid. The acidic water solution was extracted with diethyl ether and the organic layer was washed with water, dried (Na2SO4) and evaporated under reduced pressure to give 6.5 g of the title compound. was refluxed overnight the organic layer was separated To the organic layer was added a saturated sodium bicarbonate solution the aqueous layer was separated The aqueous layer was made acidic by addition of conc sulfuric acid The acidic water solution was extracted with diethyl ether the organic layer was washed with water dried (Na2SO4) evaporated under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-3-methylbenzylbromide (25 g, 0.095 mol) and potassium cyanide (16 g, 0.25 mol) in dimethylformamide (100 ml) was stirred at 90° C. for 20 h. The solvent was evaporated under reduced pressure and to the residue were added toluene and water. The organic layer was separated washed with water, separated and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride as eluent gave 8.8 g (44%) of the title compound. The solvent was evaporated under reduced pressure and to the residue were added toluene and water The organic layer was separated washed with water separated evaporated under reduced pressure Purification of the residue by column chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-3-methylbenzylcyanid (8.8 g, 42 mmol) was added to a mixture of conc sulfuric acid (50 ml) and water (60 ml) and was refluxed overnight. Water (150 ml) and diethyl ether were added and the organic layer was separated. To the organic layer was added a saturated sodium bicarbonate solution and the aqueous layer was separated. The aqueous layer was made acidic by additon of conc sulfuric acid. The acidic water solution was extracted with diethyl ether and the organic layer was washed with water, dried (Na2SO4) and evaporated under reduced pressure to give 6.5 g of the title compound. was refluxed overnight the organic layer was separated To the organic layer was added a saturated sodium bicarbonate solution the aqueous layer was separated The acidic water solution was extracted with diethyl ether the organic layer was washed with water dried (Na2SO4) evaporated under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-brom-3-methylbenzylbromide (25 g, 0.095 mol) and potassium cyanide (16 g, 0.25 mol) in dimethylformamide (100 ml) was stirred at 90° C. for 20 h. The solvent was evaporated under reduced pressure and to the residue were added toluene and water. The organic layer was separated washed with water, separated and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride as eluent gave 8.8 g (44%) of the title compound. The solvent was evaporated under reduced pressure and to the residue were added toluene and water The organic layer was separated washed with water separated evaporated under reduced pressure Purification of the residue by column chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-bromo-3-methylphenyl)acetonitril (8.0 g, 0.038 mol) was added to a mixture of water (60 ml) and sulfuric acid (50 ml) and the mixture was refluxed overnight. After cooling to room temperature water (200 ml) was added and the mixture was extracted twice with methylene chloride. The methylene chloride extracts were combined, washed twice with water, dried and evaporated under reduced pressure to give 7.9 g (90.8%) of the title compound. the mixture was refluxed overnight was added the mixture was extracted twice with methylene chloride washed twice with water dried evaporated under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-1-(bromomethyl)-3-methylbenzene (15 g, 0.057 mmol) and potassium cyanide (9.6 g, 0. 148 mol) were added to dimethylformamide (75 ml) and stirred at 90° C. overnight. The solvent was evaporated under reduced pressure and the residue partitioned between water (150 ml) and methylene chloride. The aqueous layer was extracted twice with methylene chloride, the organic extracts was separated, washed twice with water and was evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:methylene chloride (3:7) as eluent gave 8.0 g (67%) of the title compound. The solvent was evaporated under reduced pressure the residue partitioned between water (150 ml) and methylene chloride The aqueous layer was extracted twice with methylene chloride the organic extracts was separated washed twice with water was evaporated under reduced pressure Purification of the residue by column chromatography on silica gel