Dichloromethane → HCID 86758110, compound

Participants

Reaction Steps

To a solution of ethyl (Z) 3-(3-cyanophenyl)-2-butenoate (2 g, 9.3 mmol) in 50 ml carbon tetrachloride was added N-bromosuccinimide (1.74 g, 9.77 mmol) and benzoyl peroxide (40 mg, 0.165 mmol). Reaction mixture was heated to reflux and stirred over night. Reaction was allowed to cool to room temperature to which 50 ml dichloromethane was added. Organic was washed with 2×50 ml water, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude residue was chromatographed on silica gel using 2.5% EtOAc in hexane as the eluent to give ethyl (Z) 3-(3-cyanophenyl)-4-bromo-2-butenoate (0.77 g, 29%) as a clear oil (note: NOE experiment showed compound isomerized during bromination). H1NMR (CDCl3) 1.311-1.347 (t, 3H); 4.239-4.292 (m, 2H); 4.92 (s, 2H); 6.18 (s, H); 7.514-7.801 (m, 4H). ES-MS (M+H+): 293.95 and 296.0

Provenance & Evidence