N-bromobutanimide → Methyl 2-(bromomethyl)-5-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

Step 1 A suspension of methyl 5-methoxy-2-methylbenzoate (1.00 g, 5.55 mmol), N-bromosuccinimide (1.037 g, 5.83 mmol) and benzoyl peroxide (81 mg, 0.333 mmol) in tetrachloromethane (10 mL) was heated at 77° C. for 3 h. The mixture was diluted with DCM, washed with NaHCO3 (aq), dried and concentrated to provide crude methyl 2-(bromomethyl)-5-methoxybenzoate as a light yellow solid (1.435 g), used without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.48 (1H, d, J=2.64 Hz), 7.37 (1H, d, J=8.36 Hz), 7.02 (1H, dd, J=8.58, 2.86 Hz), 4.93 (2H, s), 3.95 (3H, s), 3.85 (3H, s).

Provenance & Evidence