Water → 1-Bromo-4-(propane-1-sulfonyl)benzene

HRID 1445757Notes

Reaction equation

HRID 1445757 reaction equation
[OH:1]OS([O-])=O.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=1.[OH2:18]>C1COCC1.CO>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:15][CH2:16][CH3:17])(=[O:1])=[O:18])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 179331281-Bromo-4-(propylsulfanyl)benzeneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 216127171-Bromo-4-(propane-1-sulfonyl)benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add oxone (potassium mono persulfate, 15.03 g, 24.4 mmol) in one portion to a cold (0° C.) stirred solution of 1-bromo-4-propylsulfanyl-benzene (1.881 g, 8.14 mmol) in THF (20 mL), methanol (10 mL), and water (10 mL) and slowly warm to room temperature overnight. Remove the solvents under reduced pressure and add dichloromethane and water to the residue. Separate the layers, extract the aqueous layer twice with dichloromethane, wash the organic layer with saturated aqueous sodium bicarbonate, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by flash chromatography (SiO2, elute 0% to 30% EtOAc/hexanes) to yield 1.96 g of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J=9.2 Hz, 2H), 7.74 (d, J=8.8 Hz, 2H), 3.06-3.11 (m, 2H), 1.72-1.83 (m, 2H), 1.04 (dd, J=7.2, 7.2 Hz, 3H).

Workup

  1. customRemove the solvents under reduced pressure
  2. additionadd dichloromethane and water to the residue
  3. customSeparate the layers
  4. extractionextract the aqueous layer twice with dichloromethane
  5. washwash the organic layer with saturated aqueous sodium bicarbonate
  6. dry with materialdry over anhydrous magnesium sulfate
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue
  9. washby flash chromatography (SiO2, elute 0% to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2551e7e10fa74ed3bb9c8ee1e357388e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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