Methanol → Methyl 2-(3-fluoro-4-trifluoromethylphenyl)acetate

HRID 430239Notes

Reaction equation

HRID 430239 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[CH3:16]O>S(=O)(=O)(O)O>[CH3:16][O:14][C:13](=[O:15])[CH2:12][C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:10])[F:9])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 27375913-Fluoro-4-(trifluoromethyl)phenylacetic acid

Product 1

HCID 53671544Methyl 2-(3-fluoro-4-trifluoromethylphenyl)acetateYield 97%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
25 °C

Procedure

A solution of 3-fluoro-4-(trifluoromethyl)phenylacetic acid (2.50 g, 11.25 mmol) in methanol (25 mL) was treated slowly with 4 drops of concentrated sulfuric acid. The resulting reaction mixture was heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded (3-fluoro-4-trifluoromethyl-phenyl)-acetic acid methyl ester (2.58 g, 97%) as a colorless oil: EI-HRMS m/e calcd for C10H8F4O2 (M+) 236.0460, found 236.0457.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 15 h
  4. concentrationconcentrated in vacuo
  5. customto remove methanol

Sources & evidence

ORD record
ord-b25a69609c624ade953ce6f589736237
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

Loading…