N-bromobutanimide → N-[4-(Bromomethyl)-3-(trifluoromethyl)phenyl]-2,2,2-trifluoroacetamide

Participants

Reaction Conditions

Reaction Steps

Under N2-atmosphere, a suspension of N-(4-methyl-3-trifluoromethyl-phenyl)2,2,2-trifluoro-acetamide (Stage 128.4; 5.21 g, 19.2 mmol), N-bromosuccinimide (15 g, 84 mmol) and azo-iso-butyronitrile (740 mg, 4.5 mmol) in 430 ml of CCl4 is heated to 85° C. for 15 h. The hot mixture is filtered, the solid washed with CCl4 and discarded. The filtrate is concentrated, the residue re-dissolved in CH2Cl2 (0.7 L) and washed twice with 0.5 M solution of Na2S2O3 and brine. The inorganic phases are extracted with 2 portions of CH2Cl2, the organic phases dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/CH2Cl2 1:1) yields the title compound: 1H-NMR (DMSO-d6): 11.59 (s, HN), 8.06 (d, 1H), 7.97 (dd, 1H), 7.76 (d, 1H), 4.77 (s, 2H).

Provenance & Evidence