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 under an inert atmosphere maintaining the temperature below -70° C. The mixture was stirred for 2 hours at -70° C. A solution of dimethyl disulfide (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, extracted with ether, washed with water, dried (anhydrous MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from a mixture of cyclohexane and ether to give 3,4-difluoro-2-(methylsulfenyl)benzoic acid (5.9 g) as a white solid, m.p. 149.2°-149.6° C.
Workup
- temperaturemaintaining 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 recrystallized from a mixture of cyclohexane and ether
Sources & evidence
- ORD record
- ord-b55fb0f13ee044db9b383e64aada8785
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05334753
Reaction notes
Loading…