Potassium Carbonate → [5-Fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]methanol

HRID 1921872Notes

Reaction equation

HRID 1921872 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106068384-Fluoro-2-(hydroxymethyl)phenolHCID 114599214-(4-Trifluoromethylphenyl)benzylchloride

Product 1

HCID 57971912[5-Fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4.59 g (36.9 mmol) of 5-fluoro-2-hydroxybenzyl alcohol [CAS 2357-33-7] in 200 ml of dry acetonitrile is mixed with 10.0 g (36.9 mmol) of 4-chloromethyl-4′-trifluoromethylbiphenyl and 6.13 g (44.3 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After concentration, the resulting crude product is purified by flash chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5:1). 11.8 g (32.9 mmol, 89% of theory) of the title compound are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationAfter concentration
  7. customthe resulting crude product is purified by flash chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-26aeb562fe29464785c549dac7b8e0fd
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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