Water → 1-Bromo-2-(ethylsulfanyl)benzene

HRID 1865038Notes

Reaction equation

HRID 1865038 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[SH:14].I[CH2:16][CH3:17].O>CC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 805982-Bromobenzenethiol

Product 1

HCID 130827251-Bromo-2-(ethylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add potassium carbonate (2.20 g, 15.92 mmol) to 2-bromobenzenethiol (2.00 g, 10.58 mmol) in acetone and stir at room temperature. After 10 minutes, add iodoethane (1.82 g, 11.67 mmol) with stirring. After 18 hours, add water and extract with ethyl acetate. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound.

Workup

  1. stirringwith stirring
  2. waitAfter 18 hours
  3. extractionextract with ethyl acetate
  4. washwash with water and brine
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-89b86cd333d24b55bcd65149ba025e67
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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