Water → 4-Phenylsulfonylbutyl bromide

HRID 2212066Notes

Reaction equation

HRID 2212066 reaction equation
[Na].[C:2]1([SH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11][CH2:12][CH2:13]Br.[O:15]1CCCC1.[OH2:20]>>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][S:8]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:15])=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 80561,4-DibromobutaneHCID 66586497Sodium benzenethiol

Product 1

HCID 114827894-Phenylsulfonylbutyl bromide

Procedure

A mixture of benzenethiol sodium salt (10 g, 75 mmol), 1,4-dibromobutane (20 ml) and tetrahydrofuran (100 ml) was stirred at room temperature. After 20 hours, the mixture was poured into water and extracted into i-hexane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was treated with methanol (300 ml) and a solution of Oxone™ (70 g) in water (300 ml) was added in 50-ml portions. After completion, the mixture was diluted with water and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica to give the title product.

Workup

  1. extractionextracted into i-hexane
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. additionThe residue was treated with methanol (300 ml)
  5. additiona solution of Oxone™ (70 g) in water (300 ml) was added in 50-ml portions
  6. additionAfter completion, the mixture was diluted with water
  7. extractionextracted into ethyl acetate
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified on silica

Sources & evidence

ORD record
ord-8fc3f0a9a01b43e8b494bec3c6896f2b
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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