Water → Methyl 4-Bromo-3-(bromomethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-bromo-3-methylbenzoate (Aldrich 532878, 50 g; 218 mmol; 1 eq.) in CHCl3 (1 L) were added NBS (46.6 g; 262 mmol; 1.2 eq.) in one portion and α,α′-azoisobutyronitrile (0.72 g; 4.37 mmol; 0.02 eq.) and the reaction mixture was stirred at 70° C. for 2 days. The mixture was cooled down to room temperature and water (500 mL) was added. The organic layer was washed with aq. NaHCO3 (400 mL), then brine (500 mL), dried over MgSO4 and concentrated in vacuo. The residue was washed with n-pentane (2×500 mL) to afford the title compound as a yellow solid.

Provenance & Evidence