Methanol → Methyl 2-fluoro-4-hydroxybenzoate
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a round bottom containing 2-fluoro-4-hydroxybenzoic acid (5.34 g, 34.19 mmol) (commercially available from Matrix Scientific and TCI America) was added a cold solution of MeOH (50 mL) and sulfuric acid (2.0 mL). The mixture was heated to 80° C. and monitored with TLC. After 20.5 hours, the solvent was removed, and the mixture was diluted with diethyl ether. The organic phase was washed carefully two times with saturated. aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to yield T22.1 as a white solid (5.82, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.79 (1H, s), 7.75 (1H, t, J=8.8 Hz), 6.69 (1H, dd, J=8.6, 2.3 Hz), 6.62 (1H, dd, J=13.1, 2.2 Hz), 3.78 (3H, s).
Workup
- customthe solvent was removed
- additionthe mixture was diluted with diethyl ether
- washThe organic phase was washed carefully two times with saturated
- dry with materialaqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate
- filtrationAfter filtration
- customthe organic solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-cca10f60b19244a18756b57e813b5e03
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450522B2
Reaction notes
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