Water → 2-(2-(Benzyloxy)-3,5-difluorophenyl)ethanol

HRID 921169Notes

Reaction equation

HRID 921169 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH2:9][CH2:10][OH:11])[C:3]=1[OH:12].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:12][C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[CH2:9][CH2:10][OH:11])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1172770622,4-Difluoro-6-(2-hydroxyethyl)phenol

Product 1

HCID 1183070732-(2-(Benzyloxy)-3,5-difluorophenyl)ethanolYield 79.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2,4-difluoro-6-(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)-3,5-difluorophenyl)ethanol (540 mg, 2.043 mmol, 79% yield) as viscous oil. 1H NMR (400 MHz, CDCl3) δ 7.48-7.36 (m, 5H), 6.84-6.72 (m, 2H), 5.07 (s, 2H), 3.78 (q, J=6.3 Hz, 2H), 2.84 (t, J=6.4 Hz, 2H), 1.53 (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-d8fee16aea8e4b09ba22636183e245bf
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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