Hydrogen Peroxide → HCID 21099497, compound

HRID 2376959Notes

Reaction equation

HRID 2376959 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1.OO.[OH2:19].C(OCC)(=[O:22])C>C(O)(=O)C.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1)(=[O:22])=[O:19]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 8857Ethyl AcetateHCID 21099499HCID 21099499, compound

Product 1

HCID 21099497HCID 21099497, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of {4-[(2-bromophenyl)thio]phenyl}methanol (Step 2, 5.0 g, 16.9 mmol) in acetic acid (32 mL) was added hydrogen peroxide (4.2 mL, 50.8 mmol) and the reaction stirred overnight at room temperature. Further hydrogen peroxide (4.2 mL, 50.8 mmol) and catalytic sodium tungstate were added and the reaction stirred overnight. Water and ethyl acetate were added and the aqueous layer extracted with ethyl acetate (×2). The combined organic layers were washed with sodium hydrogen carbonate and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 60% ethyl acetate/isohexane, to give {4-[(2-bromophenyl)sulfonyl]phenyl}methanol as a white solid (4.0 g, 80%). δH (400 MHz, d6 DMSO): 8.31 (1H, dd, J=1.5, 7.9 Hz), 7.85 (2H, d, J=8.3 Hz), 7.79 (1H, d, J=7.9 Hz), 7.70 (1H, t, J=7.6 Hz), 7.60 (1H, td, J=1.0, 7.7 Hz), 7.54 (2H, d, J=8.3 Hz), 5.42 (1H, t, J=5.7 Hz), 4.57 (2H, d, J=5.4 Hz); m/z (ES+) 327, 329 [MH+].

Workup

  1. stirringthe reaction stirred overnight
  2. extractionthe aqueous layer extracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with sodium hydrogen carbonate and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica
  7. washeluting with 60% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-2050c1d98b6449f6aaeeb2aedd372b36
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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