Methanol → Benzoic acid, 3-fluoro-5-iodo-4-methyl-, methyl ester
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[CH3:11])[C:5]([O:7][CH3:18])=[O:6]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
3-Fluoro-5-iodo-4-methylbenzoic acid (1.3 g, 4.6 mmol, 1 eq) was dissolved in methanol and treated with conc. Sulphuric acid (0.49 ml, 9.2 mmol, 2 eq). The above solution was stirred at 50° C. for 15 h. Later on solvent was removed and to the resulting residue diethylether was added and the organic layer was washed with 10% sodium bicarbonate solution and water. Finally, the organic layer was concentrated and purified by flash silica gel column chromatography using 240-400 silica gel and using 10% EtOAc in hexane as the eluent. Yield: 1 g (77%). 1H NMR (400 MHz CDCl3). δ 2.39 (s, 3H), 3.90 (s, 3H), 7.64 (d, 1H, J=8 Hz), 8.25 (s, 1H).
Workup
- customLater on solvent was removed and to the resulting residue diethylether
- additionwas added
- washthe organic layer was washed with 10% sodium bicarbonate solution and water
- concentrationFinally, the organic layer was concentrated
- custompurified by flash silica gel column chromatography
Sources & evidence
- ORD record
- ord-403bf3a4f26947ec87c531b6c468fd91
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048887B2
Reaction notes
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