2-bromo-2-(4-chlorophenyl)acetonitrile

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:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-trifluoromethylphenol (16.2 g., 0.1 mole) and 4-chlorophenyl-α-bromoacetonitrile (23.05 g., 0.1 mole) in methylene chloride (200 ml.) is added potassium carbonate (27.6 g., 0.2 mole). The reaction mixture is stirred and heated under reflux for six hours. The reaction mixture is then cooled to 25°C. and washed with water (300 ml.). The organic layer is dried over sodium sulfate, filtered and the solvent removed to afford crude (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile which is employed in the next step without further purification. heated under reflux for six hours washed with water (300 ml.) The organic layer is dried over sodium sulfate filtered the solvent removed

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chlorophenylacetonitrile (303.2 g., 2.0 mole) is heated to 90°C. on a steam bath and 48% hydrobromic acid (5drops) is added. Bromine (336 g., 2.1 mole) is then added dropwise to the stirred melt over a 1-hour period at 90° -95°C. The reaction mixture is heated an additional 15 minutes and then cooled. Benzene (300 ml.) is then added and 100 ml. of the benzene is removed by distillation at 80°C. The solution is cooled, filtered and the benzene removed to afford 435.5 g. of crude product which is extracted with 3 liters of hexane at 50°-55°C. Isopropanol (100 ml.) is added to the hexane solution which is then cooled to 25°C. The product is collected by filtration to afford 235.2 g. (57% yield) of 4-chlorophenyl-α-bromoacetonitrile, m.p. 46°-49°C. The reaction mixture is heated an additional 15 minutes cooled of the benzene is removed by distillation at 80°C The solution is cooled filtered the benzene removed to afford 435.5 g of crude product which is extracted with 3 liters of hexane at 50°-55°C Isopropanol (100 ml.) is added to the hexane solution which The product is collected by filtration to afford 235.2 g