1-Bromo-2-Chloroethane → Methyl 3-(1-cyanocyclopropyl)benzoate

Participants

Reaction Steps

To a solution of methyl 3-(cyanomethyl)benzoate 1 (2 g, 11.4 mmol) in DMSO (30 mL) was added NaH (60%, 913 mg, 23 mmol) in one portion. 1-bromo-2-chloroethane (1.164 mL, 11.4 mmol) was added slowly at 0° C. and stirring continued for 18 h at 25° C. The reaction was quenched with water, extracted with EtOAc, dried, and evaporated. Compound dissolved again in EtOAc and washed with NaHCO3 solution, brine, dried and concentrated to affording methyl 3-(1-cyanocyclopropyl)benzoate 33 (1.56 g, 68%). NMR (400 MHz, CDCl3) 1.47 (m, 2H), 1.78 (m, 2H), 3.93 (s, 3H), 7.45 (t, J=7.8 Hz, 1H), 7.59 (m, 1H), 7.88 (t, J=1.6 Hz, 1H), 7.97 (m, 1H).

Provenance & Evidence