Methanol → Methyl 5-fluoro-2-iodobenzoate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([I:11])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:3]=[C:4]([C:8]([I:11])=[CH:9][CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]Participants
4
Procedure
To a solution of 3-fluoro-6-iodo benzoic acid (50 g; 0.18 mol) in methanol (220 ml) were added 10 ml of sulfuric acid and the mixture heated at reflux for 24 hours. After that the solvent was evaporated and the crude mixture diluted with water and extracted with dichloromethane (3×70 ml), the organic phases were collected, washed with bicarbonate (3×100 ml), dried over sodium sulphate and concentrated to yield the desired compound (51 g).
Workup
- temperaturethe mixture heated
- temperatureat reflux for 24 hours
- customAfter that the solvent was evaporated
- additionthe crude mixture diluted with water
- extractionextracted with dichloromethane (3×70 ml)
- customthe organic phases were collected
- washwashed with bicarbonate (3×100 ml)
- dry with materialdried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bcac7cce355c41cc99d2ba55920fe80e
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062033B2
Reaction notes
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