Phenol → Benzoic acid, 4-fluoro-2-phenoxy-, methyl ester

HRID 2273697Notes

Reaction equation

HRID 2273697 reaction equation
Br[C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 7210837Methyl 2-bromo-4-fluorobenzoate

Product 1

HCID 67144536Benzoic acid, 4-fluoro-2-phenoxy-, methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 2-bromo-4-fluorobenzoate (1 g), phenol (0.565 g), cesium carbonate (1.96 g), copper(I) triflate toluene complex (0.087 g), and ethyl acetate (0.034 mL) in toluene (12 mL) was stirred at 110° C. for 24 hours. The reaction was cooled and chromatographed on silica gel with 5% ethyl acetate/hexanes.

Workup

  1. temperatureThe reaction was cooled
  2. customchromatographed on silica gel with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d78140c8dd534c4cab4a06bcfb9f0fe7
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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