Water → HCID 86717247, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[CH:4][C:3]=1[O:9][CH2:10][CH3:11].[CH3:12][S-:13].[Na+].C(I)C.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:13][CH3:12])=[CH:4][C:3]=1[O:9][CH2:10][CH3:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a stirred solution of 1-bromo-2-ethoxy-4-fluorobenzene (2.0 g) in DMF (20 mL) was added sodium methanethiolate (1.66 g). The mixture was stirred for 2 h at 65° C. The mixture was cooled to room temperature and ethyl iodide (1.3 mL) was added. The mixture was stirred at room temperature for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 1.65 g of the title compound.
Workup
- temperatureThe mixture was cooled to room temperature
- stirringThe mixture was stirred at room temperature for 1 h
- extractionthe mixture was extracted with ethyl acetate
- washThe organic phase was washed with saturated sodium chloride solution
- dry with materialdried (sodium sulfate)
- customthe solvent was removed in vacuum
Sources & evidence
- ORD record
- ord-9b131eb6c3384e248a60162024b4de03
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388177B2
Reaction notes
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