N-bromobutanimide → HCID 57155465, compound

Participants

Reaction Steps

To a solution of 2-(2-acetoxyl-4-methylphenyl)acetic acid tert-butyl ester (4.9 g, 18.5 mmol) in CCl4 (50 ml) was added N-bromosuccinimide (3.29 g, 18.5 mmol, 1 equivalents) and benzoyl peroxide (100 mg), the reaction mixture was refluxed under argon for 3 hr. The reaction mixture was then cooled to room temperature. The solid precipitate was filtered off, and washed with hexanes, the combined organic was taken to dryness, and the residue obtained was purified by chromatography (Hexanes—EtOAc, 50:1 to 40:1) to give (2-acetoxyl-4-bromomethylphenyl)acetic acid tert-butyl ester 2.467 g (38.8% yield) as an oil. 1H NMR (CDCl3) δ: 7.290 (1H, d, J=7.81 Hz), 7.230 (1H, dd, J=1.71, 7.81 Hz), 7.158 (1H, d, J=1.71 Hz), 4.467 (2H, s), 3.462 (2H, S), 2.320 (3H, s), 1.430 (9H, s) ppm. FABMS (+Ve), m/z 345 [MH+, 81Br], 343 [MH+, 79Br], 389 [MH+—C4H8, 81Br], 387 [MH+—C4H8, 79Br]. Anal. calcd. for C15H19BrO4: C, 52.5; H, 5.6; Br, 23.3. Found: C, 52.30; H, 5.50; Br, 23.44.

Provenance & Evidence