4-bromo-2-(bromomethyl)benzonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a stirred mixture of 4-Bromo-2-bromomethyl-benzonitrile Example 347A (1.00 g, 3.64 mmol) and 4-Chloro-2-iodo-phenol Example 347B (0.94 g, 3.69 mmol) in dry DMF (8.0 mL) under argon was added 95% NaH (103 mg, 4.08 mmol). The reaction mixture was stirred at room temperature for 2.5 hours and quenched with water (30 mL). The resulting mixture was extracted with ether (180 mL). The organic layer was washed with water (1×30 mL), 1N NaOH solution (1×30 mL) and brine (1×30 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 614 mg of crude 4-Bromo-2-(4-chloro-2-iodo-phenoxymethyl)-benzonitrile Example 347C which was used as is for the next transformation. quenched with water (30 mL) The resulting mixture was extracted with ether (180 mL) The organic layer was washed with water (1×30 mL), 1N NaOH solution (1×30 mL) and brine (1×30 mL) The organic layer was dried (MgSO4) filtered concentrated in vacuo

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 4-Bromo-2-methyl-benzonitrile (5.00 g, 25.5 mmol) in CCl4 (40 mL) under argon was added N-bromosuccinamide (5.00 g, 28.1 mmol) and a catalytic amount of benzoyl peroxide. This mixture was heated at 85° C. for 2 days and cooled to room temperature. The precipitate was filtered off and the cake was rinsed with CCl4 (2×10 mL). The filtrate was concentrated in vacuo to give 7.2 g crude 4-Bromo-2-bromomethyl-benzonitrile (quantitative yield) which was used without further purification. cooled to room temperature The precipitate was filtered off the cake was rinsed with CCl4 (2×10 mL) The filtrate was concentrated in vacuo

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 4-Bromo-2-methyl-benzonitrile (5.00 g, 25.5 mmol) in CCl4 (40 mL) under argon was added N-bromosuccinamide (5.00 g, 28.1 mmol) and a catalytic amount of benzoyl peroxide. This mixture was heated at 85° C. for 2 days and cooled to room temperature. The precipitate was filtered off and the cake was rinsed with CCl4 (2×10 mL). The filtrate was concentrated in vacuo to give 7.2 g crude 4-Bromo-2-bromomethyl-benzonitrile (quantitative yield) which was used without further purification. cooled to room temperature The precipitate was filtered off the cake was rinsed with CCl4 (2×10 mL) The filtrate was concentrated in vacuo

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 4-Bromo-2-methyl-benzonitrile (5.00 g, 25.5 mmol) in CCl4 (40 mL) under argon was added N-bromosuccinamide (5.00 g, 28.1 mmol) and a catalytic amount of benzoyl peroxide. This mixture was heated at 85° C. for 2 days and cooled to room temperature. The precipitate was filtered off and the cake was rinsed with CCl4 (2×10 mL). The filtrate was concentrated in vacuo to give 7.2 g crude 4-Bromo-2-bromomethyl-benzonitrile (quantitative yield) which was used without further purification. cooled to room temperature The precipitate was filtered off the cake was rinsed with CCl4 (2×10 mL) The filtrate was concentrated in vacuo