Benzyl Bromide → 1-Chloro-4-(benzylsulfonyl)benzene

HRID 748703Notes

Reaction equation

HRID 748703 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 3466721-Chloro-4-(benzylsulfonyl)benzeneYield 73%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

Sodium 4-chlorobenzenesulfinate (306 mg, 1.54 mmol) and benzyl bromide (0.18 ml, 1.54 mmol) were added to n-butanol (15 ml). The resulting mixture was stirred at 70° C. for 5 hours. After cooling to room temperature, the solvent was concentrated under reduced pressure. To the residue were added ethyl acetate. The resulting mixture was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column, whereby from the fraction eluted with hexane:ethyl acetate (=8:1), the title compound (299 mg, 73%) was obtained as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionTo the residue were added ethyl acetate
  4. washThe resulting mixture was washed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with hexane

Sources & evidence

ORD record
ord-0d3000be37954326a24a0826366d1eb2
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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