N-bromobutanimide → Methyl 2-(bromomethyl)-4-nitrobenzoate

Participants

Reaction Steps

N-Bromosuccinimide (2.18 g, 12.30 mmol) was added to a stirred solution of 2-methyl-4-nitro-benzoic acid methyl ester (2 g, 10.25 mmol) and ABCN (626 mg, 2.56 mmol) in carbon tetra-chloride (80 ml) at room temperature. The reaction was heated at reflux for 2 hrs and then allowed to cool to room temperature and stirred for 15 hrs. The solvent was evaporated in vacuo and the resulting residue filtered through a pad of silica (eluting with dichloromethane). The solvent was evaporated in vacuo to afford the title compound as a yellow solid (2.70 g, 96%). HPLC retention time 4.49 min. Mass spectrum (ES+) m/z 256 (M+H).

Provenance & Evidence