Methanethiol → 1-(4-Chlorophenyl)-2-(methylsulfanyl)ethan-1-one
Reaction equation
[OH-].[Na+].[CH3:3][SH:4].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8]>CO.O1CCCC1>[CH3:3][S:4][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
To 11.3 g (141 mmole) of 50% aqueous sodium hydroxide dissolved in 50 ml of methanol and cooled to -20° C. was added 7.7 g (160 mmole) of gaseous methyl mercaptan. To this solution was added 30.5 g (130 mmole) of 2-bromo-4'-chloroacetophenone dissolved in 40 g of tetrahydrofuran. After warming to room temperature and stirring for 30 minutes the mixture was concentrated in vacuo, partitioned between hexanes and water, dried over anhydrous magnesium sulfate, filtered, and reconcentrated in vacuo to yield 25.3 g of 2-methylthio-4'-chloroacetophenone, an oil.
Workup
- temperatureAfter warming to room temperature
- concentrationwas concentrated in vacuo
- custompartitioned between hexanes and water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-28cd0e0b900649d0881b1d79446772e3
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05798311
Reaction notes
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