Acetonitrile → HCID 738032, compound

Participants

Reaction Conditions

Reaction Steps

An oven dried flask was charged with 300 mL of tetrahydrofuran and diisopropylamine (31.4 mL, 223 mmol) and cooled to 0° C. under nitrogen. To the reaction mixture was then added butyl lithium (2.5 M in hexanes) (79.1 mL, 198 mmol) slowly by syringe over 10 minutes. The reaction mixture was then allowed to stir at 0° C. for 20 minutes. The reaction mixture was then cooled to −78° C. and acetonitrile (10.8 mL, 206 mmol) was added slowly over 5 minutes. The reaction mixture was allowed to stir for 10 minutes before 4-bromobenzonitrile (30.0 g, 165 mmol) was added as a solution in 100 mL of tetrahydrofuran over 10 minutes. The reaction mixture was allowed to proceed at −78° C. for an additional 10 minutes before being allowed to slowly warm to ambient temperature and proceed overnight. The reaction mixture was cooled to 0° C. and 200 mL of water was slowly added. The reaction mixture was stirred for 10 minutes and the solids were collected by means of vacuum filtration and dried under high vacuum. The solids were suspended in dichloromethane and the resulting solids were collected by means of vacuum filtration to obtain 3-amino-3-(4-bromophenyl)acrylonitrile (34.2 g, 153 mmol, 93.0% yield). MS (apci) m/z=222.0 (M−H).

Provenance & Evidence