3-Chlorobenzoic Acid → 4-Methylsulphinylphenacyl bromide

HRID 586613Notes

Reaction equation

HRID 586613 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:21])C=1.ClC1C=C(C=CC=1)C(O)=O>C(Cl)(Cl)Cl>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:12])=[O:21])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 70297m-Chloroperbenzoic acidHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanone

Product 1

HCID 127955374-Methylsulphinylphenacyl bromideYield 33.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2-bromo-1-(4-methylsulphanylphenyl)-1-ethanone (3.7 g, 15 mmol) in CHCl3 (50 ml) is maintained at a temperature of −5° C. A solution of m-chloroperbenzoic acid (70%, 3.7 g, 15 mmol) in CHCl3 (30 ml) cooled to 0° C. is added dropwise while maintaining an IT of −5° C. to 0° C. After stirring for ½ hour in the cold, the deposited m-chlorobenzoic acid is filtered off. The filtrate is first washed with NaHCO3 solution (8% strength, 50 ml) until acid-free and then rewashed with water (50 ml). The CHCl3 phase dried over Na2SO4 sicc. is concentrated in vacuo. A yellowish residue (1.3 g) results.

Workup

  1. additionis added dropwise
  2. temperaturewhile maintaining an IT of −5° C. to 0° C
  3. filtrationis filtered off
  4. washThe filtrate is first washed with NaHCO3 solution (8% strength, 50 ml) until acid-free and
  5. dry with materialThe CHCl3 phase dried over Na2SO4 sicc
  6. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-fd8cd5d0c77a4808bc4768150c663c77
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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