Dimethyl Disulfide → HCID 10058722, compound
Reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[F:16])[C:10]([OH:12])=[O:11].[CH3:17][S:18]SC>O1CCCC1.CCOCC>[F:6][C:7]1[C:8]([S:18][CH3:17])=[C:9]([CH:13]=[CH:14][C:15]=1[F:16])[C:10]([OH:12])=[O:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
n-Butyllithium (2.5m in hexane, 35 ml) was added with cooling to a solution of 3,4-difluorobenzoic acid (5.5 g) in dry tetrahydrofuran while maintaining the temperature below -70° C. The mixture was stirred for 2 hours at -70° C. A solution of dimethyl disulphide (19.8 g) in tetrahydrofuran was added and the mixture was stirred at -70° C. for 1.5 hours. It was allowed to warm to room temperature, diluted with ether and washed with water. The aqueous layer was acidified to pH 1 and extracted with ether, washed with water, dried (anhydrous MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was recrystallised from a mixture of cyclohexane and ether to give 3,4-difluoro-2-(methylsulphenyl)benzoic acid (5.9 g) as a white solid, m.p. 149.2°-149.6° C.
Workup
- temperaturewhile maintaining the temperature below -70° C
- stirringthe mixture was stirred at -70° C. for 1.5 hours
- temperatureto warm to room temperature
- washwashed with water
- extractionextracted with ether
- washwashed with water
- dry with materialdried (anhydrous MgSO4)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was recrystallised from a mixture of cyclohexane and ether
Sources & evidence
- ORD record
- ord-0a159a0a28234a399d90441f9bf1c52b
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05656573
Reaction notes
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