Methanol → 1-Phenyl-2-bromo-2-(4-(methylsulfonyl)phenyl)ethanone

HRID 741681Notes

Reaction equation

HRID 741681 reaction equation
[C:1]1([C:7](=[O:18])[CH:8]([Br:17])[C:9]2[CH:14]=[CH:13][C:12](SC)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.O[O:22][S:23]([O-:25])=O.[K+].[C:27]([O-])(O)=O.[Na+]>C(Cl)Cl.O.CC(O)(C)C>[C:1]1([C:7](=[O:18])[CH:8]([Br:17])[C:9]2[CH:10]=[CH:11][C:12]([S:23]([CH3:27])(=[O:25])=[O:22])=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 194267911-Phenyl-2-bromo-2-(4-(methylthio)phenyl)ethanoneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 153152121-Phenyl-2-bromo-2-(4-(methylsulfonyl)phenyl)ethanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

To a suspension of the product of step 2 (59 g, 183 mmol) in a mixture of CH2Cl2 (300 mL), MeOH (1 L), t-BuOH (350 mL) was added a suspension of oxone (248 g, 403 mmol) in 700 mL of H2O. The mixture was stirred for 1 h. Saturated NaHCO3 was added slowly until all solid dissolved. The resulting mixture was extracted with Et2O. The ether extracts were dried (Na2SO4) and concentrated to give 39.3 g of the title compound.

Workup

  1. additionwas added
  2. dissolutiondissolved
  3. extractionThe resulting mixture was extracted with Et2O
  4. dry with materialThe ether extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ebd3301c4156428e973849d59c7cfcb3
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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