Boron tribromide → 2-Methanesulfonylphenol

HRID 1093753Notes

Reaction equation

HRID 1093753 reaction equation
B(Br)(Br)Br.[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]C)(=[O:8])=[O:7]>C(Cl)Cl.O>[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])(=[O:7])=[O:8]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 27596911-Methoxy-2-(methylsulfonyl)benzene

Product 1

HCID 5989982-MethanesulfonylphenolYield 64.35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (280 mg, 1.62 mmol) was added to a cold (0-4° C.) solution of 1-methoxy-2-methylsulfanyl-benzene (100 mg, 0.64 mmol) in DCM (3 mL) and stirring was continued for 1 hr. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with saturated brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 110 mg (91.6% Yield) of 1-methanesulfonyl-2-methoxy-benzene. Boron tribromide (370 mg, 1.47 mmol) was added to a cold solution (−70° C.) solution of 1-methanesulfonyl-2-methoxy-benzene (10 mg, 0.591 mmol) in DCM (2 mL) and stirring was continued for 10 minutes. After which the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with saturated brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 65 mg (64.35% Yield) of 2-methanesulfonyl-phenol. 2-Methylsulfonyl-phenol was converted to 4-(2-methanesulfonyl-phenoxy)-piperidine hydrochloride according to Step 1 of the General Scheme).

Workup

  1. stirringAfter which the reaction mixture was stirred at ambient temperature overnight
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated brine solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76eb1558c8a24f42a43001ecb62c681e
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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