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

HRID 1860180Notes

Reaction equation

HRID 1860180 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][OH:17]>S(=O)(=O)(O)O>[C:13]([O-:15])(=[O:14])[CH3:12].[CH3:16][O:17][C:13](=[O:14])[CH2:12][C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:10])[F:11])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 2

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

Product 2

HCID 175AcetateHCID 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 with concentrated sulfuric acid (4 drops). 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 hexaneslethyl 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-b8c756157a744ef5b52cbf2307d6997d
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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