Isopropyl iodide → 2-Bromo-4-(isopropylthio)-1-methylbenzene

HRID 2390160Notes

Reaction equation

HRID 2390160 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([SH:11])[CH:7]=[CH:8][C:9]=1[CH3:10].I[CH:13]([CH3:15])[CH3:14]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([S:11][CH:13]([CH3:15])[CH3:14])[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 127220873-Bromo-4-methylbenzene-1-thiol

Product 1

HCID 585218832-Bromo-4-(isopropylthio)-1-methylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred suspension of NaH (40 mg) in anhydrous DMF (5 mL) was treated with a solution of 3-bromo-4-methylbenzenethiol (200 mg) in anhydrous DMF (3 ml). The reaction mixture was stirred for 30 minutes at RT, then 2-iodo propane (0.14 ml) was added to the reaction mixture and the reaction mixture was heated to 55° C. for 3 hours. The reaction mixture was quenched with ice and extracted with diethylether. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography (Silica gel), eluting with hexane, to give the title compounds.

Workup

  1. temperaturethe reaction mixture was heated to 55° C. for 3 hours
  2. customThe reaction mixture was quenched with ice
  3. extractionextracted with diethylether
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (Silica gel)
  7. washeluting with hexane

Sources & evidence

ORD record
ord-61052ca71ff2426d89e06eab4b24152d
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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