Bromine → 1-Bromo-1-(methylsulfonyl)-2-propanone

HRID 1188048Notes

Reaction equation

HRID 1188048 reaction equation
[CH3:1][S:2]([CH2:5][C:6](=[O:8])[CH3:7])(=[O:4])=[O:3].[Br:9]Br>CC(O)=O.ClCCl>[Br:9][CH:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6](=[O:8])[CH3:7]

Participants

5

Reactant 2

HCID 24408BromineHCID 786951-(Methylsulphonyl)acetone

Product 1

HCID 581805331-Bromo-1-(methylsulfonyl)-2-propanoneYield 42.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methanesulphonylacetone (0.5 g, 3.67 mmol) in AcOH (7.34 mL) and dichloromethane (11.02 mL) in a round bottom flask was added bromine (0.189 mL, 3.67 mmol) dropwise. The reaction mixture was stirred at rt 90 min. Solvent was removed in vacuo. The residue was taken up in ether and washed with saturated aqueous sodium bicarbonate (2×). The organics were concentrated in vacuo. 1-Bromo-1-(methylsulfonyl)propan-2-one (0.332 g, 42% yield) was isolated as an oil.

Workup

  1. customSolvent was removed in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate (2×)
  3. concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record
ord-5d2b4438727d422c94af0409a498dc35
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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