Water → 2-Bromo-4'-(methylsulfonyl)acetophenone

HRID 1979009Notes

Reaction equation

HRID 1979009 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[Al+3].[Cl-].[Cl-].[Cl-].[Br:18]Br.O>C(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 825294-MethylsulfonylacetophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cooled (−5° C.) solution of 174 g of 4-(methylsulfonyl)acetophenone in 2.5 L of CHCl3 was added 20 mg of AlCl3, followed by a solution of 40 mL of Br2 in 300 mL CHCl3. The reaction mixture was then treated with 1.5 L of water and the CHCl3 was separated. The aqueous layer was extracted with 1 L of EtOAc. The combined extracts was dried over Na2SO4 and concentrated. The crude product was recystalized from 50/50 EtOAc/hexane to give 210 g of 2-bromo-1-(4-(methylsulfonyl)phenyl)ethanone as a white solid.

Workup

  1. customthe CHCl3 was separated
  2. extractionThe aqueous layer was extracted with 1 L of EtOAc
  3. dry with materialThe combined extracts was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80f13f958ee9464c8aadfd15227874f2
Source dataset
uspto-grants-2001_05
Patent number
US06239173B1

Reaction notes

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