Methanol → 4-Fluoro-3-hydroxy-benzoic acid methyl ester
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([OH:11])[CH:4]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
4-Fluoro-3-hydroxy-benzoic acid (24.7 g, 112.8 mmol) is dissolved in methanol (300 ml) and cooled to 0° C. Thionyl Chloride (15 ml) is added dropwise and the mixture then heated at 70° C. for 60 min. The reaction mixture is concentrated in vacuo, taken up in EtOAc and washed with saturated sodium bicarbonate solution followed by saturated brine. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a white solid.
Workup
- temperaturethe mixture then heated at 70° C. for 60 min
- concentrationThe reaction mixture is concentrated in vacuo
- washwashed with saturated sodium bicarbonate solution
- dry with materialThe organic layer is dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-7b413d1ecafc41d3a03c3c2619d6bed1
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039455B2
Reaction notes
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