Water → 4-Bromo-2-chloro-1-methanesulfonylbenzene

HRID 732760Notes

Reaction equation

HRID 732760 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([Cl:10])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1.[OH2:22]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:9])(=[O:19])=[O:22])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 573461311-Bromo-3-chloro-4-(methylthio)benzene

Product 1

HCID 230930614-Bromo-2-chloro-1-methanesulfonylbenzeneYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 4-bromo-2-chloro-1-methylsulfanyl-benzene (4.8 g, 20 mmol) and mCPBA (20 g, 80 mmol) in dichloromethane (100 mL). Stir for 2 hours. Dilute with dichloromethane (300 mL) and water (100 mL). Separate the organic layer and wash with aqueous saturated NaHCO3 (2×100 mL) and brine (100 mL). Dry with MgSO4, filter and concentrate in vacuo. Wash the solid with ether (2×10 mL) and dichloromethane (10 mL) to give 1.7 g of the title compound (31%).

Workup

  1. customSeparate the organic layer
  2. washwash with aqueous saturated NaHCO3 (2×100 mL) and brine (100 mL)
  3. dry with materialDry with MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. washWash the solid with ether (2×10 mL) and dichloromethane (10 mL)

Sources & evidence

ORD record
ord-484835b8cc9f47a8a9979ac682e229b5
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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