Dichloromethane → 1-Bromo-4-(methylsulphinyl)benzene

HRID 840473Notes

Reaction equation

HRID 840473 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:21])C=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:9])=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 660374-BromothioanisoleHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 30139581-Bromo-4-(methylsulphinyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.06 g (20 mmol) of 4-bromothioanisole and 75 ml of dichloromethane were introduced into a round-bottomed flask and 6.3 g (20 mmol) of meta-chloroperbenzoic acid were added. Stirring was carried out at room temperature for four hours and the reaction mixture was poured into water. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and heptane (70/30). After evaporating the solvents, 1.22 g (28%) of the expected sulfoxide, with a melting point of 80°-81° C., was recovered.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica column
  6. washeluted with a mixture of dichloromethane and heptane (70/30)
  7. customAfter evaporating the solvents, 1.22 g (28%) of the expected sulfoxide
  8. customwith a melting point of 80°-81° C., was recovered

Sources & evidence

ORD record
ord-9b59cbe9856d4a9194a151eb7fe66007
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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