Sodium methanethiolate → 2-Chloro-4-iodobenzyl methyl sulfide
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.[CH3:11][S-:12].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:11][S:12][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([I:10])=[CH:9][C:2]=1[Cl:1]Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-chloro-4-iodobenzyl bromide (4.82 g, 14.54 mmol) in N,N-dimethylformamide (30 mL) was treated with sodium thiomethoxide (2.04 g, 29.08 mmol). After the addition, the solution became cloudy and turned to a yellow color. The resulting reaction mixture was stirred for 3 h at 25° C. The reaction mixture was then diluted with ethyl acetate (100 mL). The organic layer was washed successively with water (2×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 2-chloro-4-iodobenzyl methyl sulfide (4.24 g, 97%) as a colorless oil which was used without further purification: EI-HRMS m/e calcd for C8H8CIIS (M+) 297.9080, found 297.9078.
Workup
- additionAfter the addition
- customThe resulting reaction mixture
- washThe organic layer was washed successively with water (2×100 mL)
- dry with materiala saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5536b223004b41d781ecb6ecdc56b4c2
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353111B1
Reaction notes
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