3-Hydroxybenzyl alcohol → 3-(Bromomethyl)phenol

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).

1. customTo a 50 mL RB flask fitted with magnetic stirrer
2. customwas brought to 0° C.
3. additionAfter addition
4. waitAfter 1 h
5. washthe organic layer was washed with water (20 mL)
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. customthe solvent was removed under reduced pressure
8. customThe product was obtained as brown solid

ORD record

ord-bb5a8d31294f48cb971616a97627304e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2