Methanol → Methyl 2-(3,4-difluorophenyl)acetate

HRID 1860114Notes

Reaction equation

HRID 1860114 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69571(3,4-Difluorophenyl)acetic acid

Product 1

HCID 18187749Methyl 2-(3,4-difluorophenyl)acetateYield 95.2%

Procedure

A solution of (3,4-difluoro-phenyl)-acetic acid (5.0 g, 0.029 mol) in methanol (30.0 mL) was treated with a catalytic amount of sulfuric acid. The reaction mixture was refluxed for 4 h. The reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded (3,4-difluoro-phenyl)-acetic acid methyl ester (5.15 g, 95.2%) as a clear oil: EI-HRMS m/e calcd for C9H8F2O2 (M+) 186.0493, found 186.0492.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-afcf7f92e9414699a39842cd7069c48e
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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