Sodium Carbonate → HCID 21183151, compound

HRID 848986Notes

Reaction equation

HRID 848986 reaction equation
[Cl:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4](SC)[CH:5]=[CH:6][C:7]=1[Br:8].Cl[C:18]1C=CC=C(C(OO)=O)C=1.[S:28](=[O:31])(O)[O-:29].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([S:28]([CH3:18])(=[O:31])=[O:29])[CH:5]=[CH:6][C:7]=1[Br:8]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 21183158HCID 21183158, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 21183151HCID 21183151, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.5 g (8.0 mmol) of 3-chloro-4-bromo-2-phenyl(methylthio)benzene in 75 mL of dichloromethane was cooled with an ice bath and 5.7 g of meta-chloroperbenzoic acid was added in small portions with cooling and stirring. The mixture was allowed to warm to ambient temperature and stir overnight and was then heated to reflux for a short time. An aqueous solution of sodium bisulfite was added and the mixture was made basic with sodium carbonate. The organic phase was separated, washed with dilute aqueous sodium bicarbonate solution, water, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated by evaporation under reduced pressure. The 3.0 g of residue was the title compound as a low melting white solid.

Workup

  1. temperaturewith cooling
  2. stirringstir overnight
  3. temperaturewas then heated
  4. temperatureto reflux for a short time
  5. customThe organic phase was separated
  6. washwashed with dilute aqueous sodium bicarbonate solution, water, and saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7e1140aedac74de48eee6022959a6bc1
Source dataset
uspto-grants-2000_01
Patent number
US06010981

Reaction notes

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