Water → 4,5-Difluoro-2-(2-hydroxyethyl)phenol
Reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][CH2:10][OH:11])=[C:4]([O:12]C)[CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:12])=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(4,5-difluoro-2-methoxyphenyl)ethanol (800 mg, 4.25 mmol) in DCM (25 mL) at 0° C. was added 1M BBr3 (17.01 mL, 17.01 mmol) solution and the resulting mixture was allowed to warm to room temp and stir for 4 h. Then, water (dropwise) was added and after the bubbling stops mixture was diluted with DCM and washed with water, dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (5-70%, EtOAc/hexane) to afford 4,5-difluoro-2-(2-hydroxyethyl)phenol (450 mg, 2.58 mmol, 60.8% yield) as clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 6.93-6.84 (m, 1H), 6.75 (dd, J=11.5, 7.1 Hz, 1H), 4.03-3.96 (m, 2H), 2.85 (t, J=5.2 Hz, 2H).