Hydrogen Bromide → 4-(Benzenesulfonyl)phenol

HRID 1463276Notes

Reaction equation

HRID 1463276 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.Br>C(O)(=O)C>[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

4

Reactant 2

HCID 260Hydrogen BromideHCID 43517701-Methoxy-4-(phenylsulfonyl)benzene

Product 1

HCID 3438044-(Benzenesulfonyl)phenolYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 24.8 g (100 mmole) of the compound obtained in step 1 dissolved in 50 ml of acetic acid was added 40% HBr, which was heated to reflux for 8 hours. The reaction solution was poured into ice-water. The resultant solution was extracted with ethyl acetate (100 ml×3), dried over Na2SO4 and concentrated to obtain residue, which was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (1:1) to obtain 23.0 g (yield 100%) of the title compound containing a portion of orthoisomer (approximately one-eighth).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 hours
  3. extractionThe resultant solution was extracted with ethyl acetate (100 ml×3)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain residue, which
  7. customwas purified by silica gel column chromatography
  8. additiona mixture of hexane and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-45b3f712f18e4b6fa95525068d76148f
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

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