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

Participants

Reaction Conditions

Reaction Steps

Under N2, to a solution of methyl 4-bromo-3-methylbenzoate (Aldrich 532878, 50.0 g, 218.3 mmol) in CHCl3 (1 L) were added NBS (46.6 g, 261.9 mmol) in one portion and α,α′-azoisobutyronitrile (0.72 g, 4.37 mmol). The mixture was stirred at 70° C. for 2 days. The reaction mixture was cooled to RT and water (500 mL) was added. The organic layer was washed with a saturated aqueous solution of NaHCO3 (500 mL), water (340 mL), then brine (500 mL), dried over MgSO4 and concentrated affording the title compound as a yellow solid. It was washed with pentane (2×500 mL) affording the title compound as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.24 (d, J=1.91 Hz, 1H), 7.88-7.82 (m, 2H), 4.87 (s, 2H), 3.91 (s, 3H). HPLC (Method A) Rt 4.44 min (Purity: 97.9%).

Provenance & Evidence