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 (O5.007; 3.0 g) was dissolved in absolute DMF (75 ml). Then iodomethane (3.6 ml) was added while stirring, followed by finely powdered potassium carbonate (6.3 g). After stirring at 40° C. for 5 hours, the mixture was cooled and admixed with water (250 ml). The mixture was then extracted four times with ether (100 ml). The combined extracts were each washed once with 1 N sodium hydroxide solution (75 ml) and water (100 ml), dried over magnesium sulfate, filtered and concentrated. 2.9 g of the desired compound were obtained.
Workup
- stirringAfter stirring at 40° C. for 5 hours
- temperaturethe mixture was cooled
- extractionThe mixture was then extracted four times with ether (100 ml)
- washeach washed once with 1 N sodium hydroxide solution (75 ml) and water (100 ml)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fc423c61f2d04fabbf3bb964134d4f79
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076336B2
Reaction notes
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