1-(3-Bromo-4-fluorophenyl)ethan-1-one → 1-[3-Bromo-4-(methylthio)phenyl]ethanone
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][S-:13].[Na+]>CC(N(C)C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[S:13][CH3:12]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
The 1-(3-bromo-4-fluorophenyl)ethanone (2.00 g, 9.20 mmol) and sodium thiomethoxide (0.710 g, 10.1 mmol) was dissolved in dimethylacetamide (4.6 mL) and the slurry was heated at 120° C. in a microwave reactor for 1 h. The reaction mixture was diluted with water (30 mL) and the mixture was extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (1×75 mL) and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica gel, 0 to 75% EtOAc:hexanes) to give 1-(3-bromo-4-(methylthio)phenyl)ethanone. Mass Spectrum (ESI) m/e=245.1 (M+1).
Workup
- extractionthe mixture was extracted with EtOAc (2×100 mL)
- washThe combined organic layers were washed with water (1×75 mL)
- dry with materialdried over magnesium sulfate
- customThe crude product was purified by medium pressure chromatography (silica gel, 0 to 75% EtOAc:hexanes)
Sources & evidence
- ORD record
- ord-c6dce9f48dc7456f9721356310978a3a
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940724B2
Reaction notes
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