Water → 2-(6-(Benzyloxy)-2,3-difluorophenyl)ethanol

HRID 921177Notes

Reaction equation

HRID 921177 reaction equation
[F:1][C:2]1[C:3]([CH2:10][CH2:11][OH:12])=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].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:4]1[C:3]([CH2:10][CH2:11][OH:12])=[C:2]([F:1])[C:7]([F:8])=[CH:6][CH:5]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1172770673,4-Difluoro-2-(2-hydroxyethyl)phenol

Product 1

HCID 1183070642-(6-(Benzyloxy)-2,3-difluorophenyl)ethanolYield 83.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,4-difluoro-2-(2-hydroxyethyl)phenol (460 mg, 2.64 mmol) in Acetone (10 mL) was added K2CO3 (730 mg, 5.28 mmol) followed by (bromomethyl)benzene (0.471 mL, 3.96 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-(6-(benzyloxy)-2,3-difluorophenyl)ethanol (580 mg, 2.195 mmol, 83% yield) as viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.46-7.34 (m, 5H), 6.99 (q, J=9.1 Hz, 1H), 6.67-6.59 (m, 1H), 5.09 (s, 2H), 3.86 (q, J=6.4 Hz, 2H), 3.05 (td, J=6.5, 1.7 Hz, 2H).

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-fff48e462f624522bc74fc911f428474
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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