Methyl iodide → (4-Bromo-3-methylphenyl)(methyl)sulfane

HRID 422555Notes

Reaction equation

HRID 422555 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][C:3]=1[CH3:9].[H-].[Na+].I[CH3:13]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:13])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 156611054-Bromo-3-methylbenzene-1-thiol

Product 1

HCID 26370189(4-Bromo-3-methylphenyl)(methyl)sulfaneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-3-methylbenzenethiol (5.47 g, 26.9 mmol) in DMF (25 mL) was added NaH (0.743 g, 32.3 mmol) at RT. After 15 minutes at RT, the solution was cooled to 0° C. and iodomethane (2.02 ml, 32.3 mmol) was added. The cooling bath was removed and the mixture was allowed to warm up to RT. After 1 hour, water was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 5.81 g of (4-bromo-3-methylphenyl)(methyl)sulfane as a pale yellow oil.

Workup

  1. customThe cooling bath was removed
  2. temperatureto warm up to RT
  3. waitAfter 1 hour
  4. additionwater was added
  5. extractionthe mixture was extracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-681b44b80a914c4ea9a700a725aa2305
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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