3-Hydroxybenzyl alcohol → 3-(Bromomethyl)phenol

Participants

Reaction Steps

To a 50 mL RB flask fitted with magnetic stirrer was charged 15 mL of dichloromethane. To the stirred solvent was added 3-hydroxymethyl-phenol (0.5 g, 4.03 mmol). The RM was brought to 0° C. and phosphorous tribromide (1.6 g, 0.56 mL, 6.04 mmol) was added drop wise. After addition, the RM was stirred at RT for 1 h. After 1 h, the RM was diluted with dichloromethane (25 mL) and the organic layer was washed with water (20 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as brown solid. (0.65 g, yield: 86.3%); MS (ESI, 120 eV): m/z=187.0 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 7.10-7.15 (t, 1H), 6.86-6.89 (d, 1H), 6.80 (d, 1H), 6.67-6.71 (m, 1H), 4.35-4.36 (d, 2H), 3.80-3.94 (bro s, 1H).

Provenance & Evidence