Water → 4-(Benzenesulfonyl)phenol

HRID 2224057Notes

Reaction equation

HRID 2224057 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.O>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 43517701-Methoxy-4-(phenylsulfonyl)benzene

Product 1

HCID 3438044-(Benzenesulfonyl)phenolYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Benzenesulfonyl-4-methoxy-benzene (5.92 g, 23.8 mmol) was dissolved in methylene chloride and stirred. A solution of BBr3 (6.77 g, 71.68 mg) in 120 mL of methylene chloride was added dropwise to the reaction mixture, after which the mixture was stirred for 4 hours at room temperature. Water (150 mL) was then added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted three times with 45 mL methylene chloride, and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (30-50% EtOAc in hexanes) to afford 5.348 g of 4-benzenesulfonyl-phenol (22.8 mmol, 99%) as an oil. MS: 235 (M+H)+.

Workup

  1. stirringafter which the mixture was stirred for 4 hours at room temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted three times with 45 mL methylene chloride
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (30-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c32422dc0e854be5bf7810b97e5f2bbd
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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