Water → Methyl 3-methoxy-5-(pentafluorosulfanyl)benzoate
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5](O)=[O:6].IC.[C:19](=O)([O-])[O-].[K+].[K+].O.CN([CH:29]=[O:30])C>>[CH3:19][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([O:30][CH3:29])=[O:6]Participants
6
Procedure
3-Hydroxy-5-(pentafluorosulfanyl)benzoic acid (84 mg) was dissolved in absolute DMF (5 ml). Iodomethane (100 μl) was then added while stirring, followed by finely powdered potassium carbonate (175 mg). After stirring at 40° C. for 3 hours, the mixture was cooled and admixed with water (20 ml). The mixture was then extracted four times with ether (10 ml). The combined extracts were washed once each with 1N sodium hydroxide solution (10 ml) and water (10 ml), dried over magnesium sulfate, filtered and concentrated. 81 mg of the desired compound were obtained.
Workup
- stirringAfter stirring at 40° C. for 3 hours
- temperaturethe mixture was cooled
- extractionThe mixture was then extracted four times with ether (10 ml)
- washThe combined extracts were washed once each with 1N sodium hydroxide solution (10 ml) and water (10 ml)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9d0d1621d1a641f883252d0b69e7feb2
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466169B2
Reaction notes
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