Methanol → Methyl 2-(4-chloro-2-fluorophenyl)acetate

HRID 546878Notes

Reaction equation

HRID 546878 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[C:8]([F:16])[CH:7]=1.[CH3:17]O>>[CH3:17][O:14][C:13](=[O:15])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][C:8]=1[F:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2757563(4-Chloro-2-fluorophenyl)acetic acid

Product 1

HCID 57443493Methyl 2-(4-chloro-2-fluorophenyl)acetateYield 96%

Procedure

Thionyl chloride (0.94 mL, 0.0129 mol) was added dropwise to a solution of (4-chloro-2-fluoro-phenyl)acetic acid (2.03 g, 0.0108 mol) in methanol (100 mL) at 0° C., and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel chromatography (n-hexane/ethyl acetate=1/0 to 3/1) to give the title compound (2.11 g, 96%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-77d81a629edf472eb5dc9383aed844e0
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…