1-Methoxy-3-(methylsulfonyl)benzene → 3-(Methylsulfonyl)phenol

HRID 1798799

Reaction equation

HRID 1798799 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:4]=1>Br.C(O)(=O)C>[CH3:12][S:9]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1)(=[O:10])=[O:11]

Participants

4

Reactant 1

HCID 2596501-Methoxy-3-(methylsulfonyl)benzene

Product 1

HCID 6375563-(Methylsulfonyl)phenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

1-Methoxy-3-(methylsulfonyl)benzene (300 mg, 1.61 mmol) was suspended in 1.6 mL aqueous hydrobromic acid (48% w/w) and 1.6 mL acetic acid. The mixture was heated under reflux for 24 hours. The reaction was cooled back to room temperature and concentrated. The residue was purified by column chromatography through a 40 gram biotage silica gel cartridge eluting with 40-70% ethyl acetate/hexanes (gradient) to give the product as white solid. LRMS calc: 172.0; obs: 173.2 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography through a 40 gram biotage silica gel cartridge
  5. washeluting with 40-70% ethyl acetate/hexanes (gradient)

Sources & evidence

ORD record
ord-11b48ec471dc4eb293cd2916ea000e55
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Linked notes

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