Methanol → Methyl 4,5-difluoro-2-hydroxybenzoate
Reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:12])[CH:3]=1.OS(O)(=O)=O.[CH3:18]O>>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[C:4]([OH:12])[CH:3]=1Participants
4
Procedure
A mixture of 4,5-difluoro-2-hydroxybenzoic acid (20 mmol), methanol (100 ml) and concentrated H2SO4 (5 ml) was refluxed for 48 h. Then, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate, washed with brine and a saturated NaHCO3 solution and neutralized with citric acid. The organic layer was dried over MgSO4 and concentrated in vacuo to give the product. Yield: 2.8 g (97% purity, 74% yield).
Workup
- temperaturewas refluxed for 48 h
- concentrationThen, the reaction mixture was concentrated
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with brine
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated in vacuo
- customto give the product
Sources & evidence
- ORD record
- ord-a95824d141a64b4eb3367fc72a420a56
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716293B2
Reaction notes
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