2-Methylcyclohexanone → 2-Bromo-2-methylcyclohexanone

Participants

Reaction Steps

A solution of 15 g (0.134 mol) of 2-methyl-1-cyclohexanone (7) and 23.84 g (0.134 mol) of N-bromosuccinimide in 150 mL of carbon tetrachloride was stirred and heated to reflux for 12 h under argon. The mixture was cooled to room temperature, filtered through Celite to remove succinimide and the filter cake was washed with 150 mL of ether. The filtrate was concentrated to give 25.6 g (100% yield) of 2-bromo-2-methyl-1-cyclohexanone. 1H NMR δ 3.21 (td, J=16 Hz, 8 Hz, 1 H, CH--CO), 2.36 (m, 2 H), 2.06 (m, 2 H), 1.82 (s, 3 H, Me), 1.77 (m, 2 H), 1.62 (m, 1 H).

Provenance & Evidence