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

HRID 1597488Notes

Reaction equation

HRID 1597488 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].[Cl-].[Al+3].[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)acetophenoneYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-(methylsulfonyl)acetophenone (4.85 g, 24.5 mmol) in CHCl3 (70 mL) was added aluminum chloride (1 mg) and bromine (1.1 mL) in CHCl3 (8.5 mL) dropwise. The mixture was stirred overnight, and poured into water. The whole was extracted with ethyl acetate (50 mL×2), the combined organic layer was dried over MgSO4, and concentrated in vacuo. The resulting residue was recrystallized from ethyl acetate/hexane (1/1) to give the subtitle compound (5.28 g, 78% yield).

Workup

  1. extractionThe whole was extracted with ethyl acetate (50 mL×2)
  2. dry with materialthe combined organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was recrystallized from ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-1c28cef756954a7f9fd1e8848d8b8e72
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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