Water → (4-Bromo-2-methoxyphenyl)(methyl)sulfane

HRID 1098997Notes

Reaction equation

HRID 1098997 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:11])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 47132014-Bromo-2-methoxybenzenethiol

Product 1

HCID 57167258(4-Bromo-2-methoxyphenyl)(methyl)sulfaneYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-methoxybenzenethiol (1.21 g, 5.52 mmol) in DMF (5 mL) was added potassium carbonate (2.29 g, 16.5 mmol) under argon. The resulting mixture was stirred for 10 min, and then iodomethane (3.44 mL, 55.2 mmol) was slowly added over 2 min. The resulting mixture was stirred at r.t. overnight. Then the reaction mixture was poured into water (75 ml), and extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated, the residue was purified by flash chromatography on silica gel with n-heptane/ethyl acetate (7:3) to give 920 mg (72%) of the subtitle compound.

Workup

  1. stirringThe resulting mixture was stirred at r.t. overnight
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. customthe solvent was evaporated
  5. customthe residue was purified by flash chromatography on silica gel with n-heptane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-f9987c0fe7ee4e389c943e41ee163ca0
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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