[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([CH2:10][CH2:11][OH:12])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CC(C)=O>[CH2:20]([O:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([F:1])=[CH:3][C:4]=1[CH2:10][CH2:11][OH:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
To a solution of 4,5-difluoro-2-(2-hydroxyethyl)phenol (450 mg, 2.58 mmol) in acetone (10 mL) was added K2CO3 (714 mg, 5.17 mmol) followed by (bromomethyl)benzene (0.461 mL, 3.88 mmol) and the resulting mixture was stirred at room temp for 16 h. Water was then added and the mixture was extracted with ethyl acetate, dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (5-30% EtOAc/hexane) to afford 2-(2-(benzyloxy)-4,5-difluorophenyl)ethanol (580 mg, 2.195 mmol, 85% yield) as viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.48-7.33 (m, 5H), 7.10-7.01 (m, 1H), 6.78 (dd, J=12.1, 6.7 Hz, 1H), 5.05 (s, 2H), 3.85 (q, J=6.0 Hz, 2H), 2.90 (t, J=6.4 Hz, 2H), 1.52 (t, J=5.5 Hz, 1H).
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