Water → 1-Bromo-4-(propylsulfanyl)benzene

HRID 748948Notes

Reaction equation

HRID 748948 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:12][CH2:13][CH3:14].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 660494-Bromothiophenol

Product 1

HCID 179331281-Bromo-4-(propylsulfanyl)benzeneYield 110.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-bromo-benzenethiol (2.0 g, 10.6 mmol) in dry dimethylformamide (50 mL) and cool to 0° C. under nitrogen. Add sodium hydride (305 mg, 12.7 mmol) in portions. After the vigorous gas evolution stops, add 1-bromo-propane (1.4 mL, 15.9 mmol) and stir the reaction mixture overnight at room temperature. Slowly pour the reaction into water (400 mL) and extract with diethyl ether (2×150 mL). Wash the combined organic layers with water (100 mL). Dry the organic layer with sodium sulfate, filter and concentrate in vacuo to yield 2.7 g of 1-bromo-4-propylsulfanyl-benzene (quantitative yield).

Workup

  1. additionSlowly pour
  2. extractionextract with diethyl ether (2×150 mL)
  3. washWash the combined organic layers with water (100 mL)
  4. dry with materialDry the organic layer with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0e385ea03ed44f68b2e9e47feb698014
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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