Potassium Carbonate → {2-[(4-Bromophenyl)(difluoro)methoxy]-5-fluorophenyl}methanol

HRID 1672637Notes

Reaction equation

HRID 1672637 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][OH:10])[CH:3]=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](Br)([F:20])[F:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH2:9][OH:10])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106068384-Fluoro-2-(hydroxymethyl)phenolHCID 223280691-Bromo-4-(bromodifluoromethyl)benzene

Product 1

HCID 57864347{2-[(4-Bromophenyl)(difluoro)methoxy]-5-fluorophenyl}methanolYield 35.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 1.17 g (8.23 mmol) of 4-fluoro-2-(hydroxymethyl)phenol from Example 34A, 2.59 g (12.63 mmol) of 1-bromo-4-[bromo(difluoro)methyl]benzene from Example 33A and 1.25 g (9.06 mmol) of potassium carbonate in 10 ml of 2-propanol is heated to reflux for 12 hours. The mixture is then concentrated to dryness. The residue is suspended in methylene chloride, absorbed on silica gel, dried in vacuo and purified by chromatography (mobile phase: cyclohexane/ethyl acetate 10:1, then 100% ethyl acetate). 1.02 g (2.95 mmol, 35% yield) of the title compound are obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. customabsorbed on silica gel
  5. customdried in vacuo
  6. custompurified by chromatography (mobile phase

Sources & evidence

ORD record
ord-f6737058979b48efa487ee9e1356f97b
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

Loading…