1-Bromo-3-chloropropane → 1-[4-((3-Chloropropyl)thio]-3-methoxyphenyl]ethanone
Reaction equation
[CH3:1][C:2]([C:4]1[CH:10]=[C:9]([O:11][CH3:12])[C:7](=[S:8])[CH2:6][CH:5]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23].C1CCCCC1>CC(C)=O>[Cl:23][CH2:22][CH2:21][CH2:20][S:8][C:7]1[CH:6]=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[CH:10][C:9]=1[O:11][CH3:12]Participants
Procedure
A mixture of 1-(4-thio-3-methoxyphenyl)ethanone (10.0 g, 54.9 mmol), potassium carbonate (9.0 g, 65.1 mmol), and acetone (100 ml) was stirred at reflux under nitrogen for 30 minutes. The reaction was cooled to ambient temperature and a solution of 1-bromo-3-chloropropane (6.5 ml, 9.5 g, 60.4 mmol) dissolved in acetone (25 ml) was dripped into the reaction. After complete addition, the reaction was heated to reflux and stirred under nitrogen for 17 hours. After the reaction was carried to substantial completion, the reaction mixture was filtered and the resulting filter cake was washed with acetone. The filtrate was concentrated to provide an amber oil. A small sample was solidified by trituration with hot cyclohexane to provide 1-[4-[(3-chloropropyl)thio]-3-methoxyphenyl]ethanone as a yellow solid, 11.7 g, m.p.=53°-55° C.
Workup
- temperatureat reflux under nitrogen for 30 minutes
- customwas dripped into the reaction
- additionAfter complete addition
- temperaturethe reaction was heated
- temperatureto reflux
- stirringstirred under nitrogen for 17 hours
- filtrationthe reaction mixture was filtered
- filtrationthe resulting filter cake
- washwas washed with acetone
- concentrationThe filtrate was concentrated
- customto provide an amber oil
Sources & evidence
- ORD record
- ord-ba166da3d81b4d55a1d1abb7d858f61b
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05854263
Reaction notes
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