4-Bromo-2-fluorotoluene → 4-Bromo-1-methyl-2-(methylsulfanyl)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4](F)[CH:3]=1.C(S)[CH2:11][S:12]([O-])(=O)=O.[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([S:12][CH3:11])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a stirred solution of 4-bromo-2-fluoro-1-methyl-benzene (3 mL, 26.3 mmol) in DMF (15 mL) was added MeSNa (1.84 g, 26.3 mmol). After the addition, the reaction mixture was stirred at 90° C. overnight. TLC (petroleum) showed the reaction was complete. Then the mixture was poured into aq. NaHCO3 (10 mL), extracted with EtOAc (20 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over sodium sulfate and concentrated in vacuum. The residue was purified by a silica gel column chromatography (petroleum) to give 4-Bromo-1-methyl-2-methylsulfanyl-benzene (4 g, 68%) as a yellow liquid.
Workup
- additionAfter the addition
- extractionextracted with EtOAc (20 mL×2)
- washThe combined organic layers were washed with brine (50 mL×3)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuum
- customThe residue was purified by a silica gel column chromatography (petroleum)
Sources & evidence
- ORD record
- ord-8675fac59cd04c5482098f0fc39064b5
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916593B2
Reaction notes
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