Bromoacetyl bromide → HCID 19756863, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (-10° C.), stirred suspension of 2-amino-2-fluorobenzophenone (19.40 g, 0.090 mol) in dichloromethane (130 mL) and water (10 mL) was added a solution of bromoacetylbromide (9.0 mL, 0.104 mol) in dichloromethane (30 mL), keeping the temperature of the reaction mixture at -10° C. After addition the reaction mixture was stirred whilst warming to room temperature (21/2hours). The organic layer was collected, washed with water (2×100 mL) then concentrated to approximately 70 mL. Hexane (70 mL) was added and the required product collected by filtration (25.6 g, 83%): mp 120°-121° C. Rf 0.30 in diethyl ether/n-hexane (1:1) on silica; 1H NMR (CDCl3) δ4.05 (2H,s), 7.10-7.64 (7H, m), 8.70 (1H, d, J=8 Hz), 11.95 (1H, broad s); MS, m/z 335 (M+ ). Anal. Calcd. for C15H11BrFNO2 :C, 53.59; H, 3.30; N, 4.17. Found: C, 53.32; H, 3.33; N, 4.00.

Provenance & Evidence