1-Bromo-1-chloroethane → 1-(3,4-Dichlorophenyl)cyclopropanecarbonitrile

Participants

Reaction Steps

To a stirred mixture of 3,4-Dichloro-phenylacetonitrile (4.65 g. 25 mmol) triethylbenzylammonium chloride (0.2 g) and 1-bromochoroethane (4.2 ml, 50 mmol), 50% sodium hydroxide (16 ml, 200 mmol) was added dropwise at 50° then the reaction was stirred at 50° for 10 hrs. After cooling to rt, the reaction mixture was diluted with water and extracted with EtOAc (×3). The layers were separated, washed with water (×3) and brine, then dried over MgSO4. Evaporation of the solvent under reduced pressure afforded the title compound (5.43 g) which was then recrystallized from Et2O/hexanes as a pale pink solid (4.49 g, 85%). Lc/MS(ES) m/e 212 [M+H]+.

Provenance & Evidence