Methanol → Methyl 3-fluoro-4-hydroxybenzoate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:17])=[O:6]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a round bottom flask containing 3-fluoro-4-hydroxybenzoic acid (5.03 g, 32.22 mmol) (commercially available from Aldrich) was added a cold solution of MeOH (50.0 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 twice with saturated aqueous NaHCO3 and once with brine. The organic phase was then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to afford T25.1 as a white solid (4.79 g, 87% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (2H, m), 7.06 (1H, t, J=8.4 Hz), 5.62 (1H, d, J=4.3 Hz), 3.91 (3H, s).
Workup
- customthe solvent was removed
- additionthe mixture was diluted with diethyl ether
- washThe organic phase was washed carefully twice with saturated aqueous NaHCO3 and once with brine
- dry with materialThe organic phase was then dried over anhydrous sodium sulfate
- filtrationAfter filtration
- customthe organic solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-93c9279afb2546ec9bed35115f708866
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450522B2
Reaction notes
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