Water → 2-(2-(Benzyloxy)-4,5-difluorophenyl)ethanol

HRID 921184Notes

Reaction equation

HRID 921184 reaction equation
[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

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1172770664,5-Difluoro-2-(2-hydroxyethyl)phenol

Product 1

HCID 1183070102-(2-(Benzyloxy)-4,5-difluorophenyl)ethanolYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then purified by Biotage (5-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-06930c1c664545fba474a30d3bd6d562
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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