p-Bromobenzenesulfonyl chloride → 1-((4-Bromophenyl)sulfonyl)azetidine

HRID 1710388Notes

Reaction equation

HRID 1710388 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1>ClCCl.C(=O)([O-])[O-].[K+].[K+]>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 10422Azetidine

Product 1

HCID 72132421-((4-Bromophenyl)sulfonyl)azetidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

4.09 g of azetidine are dissolved in a two-phase solvent system of 200 ml of dichloromethane and 130 ml of an aqueous potassium carbonate solution (strength 4.0 M). Subsequently, a solution of 15.25 g of commercially available 4-bromo-benzenesulfonyl chloride in 70 ml of dichloromethane is slowly added to the reaction mixture. Thereafter, the mixture is vigorously stirred for 17 hours at room temperature. For extraction, 200 ml of dichloromethane and 100 ml of water are added. The organic layer is dried using Na2SO4, filtered with suction, and concentrated in vacuo to yield 15.22 g of the title compound as a colorless, amorphous solid of m.p. 145° C. ESI-MS: 276.1/278.0 (MH+, 100%:95%). TLC: Rf=0.59 (dichloromethane/ethanol 10:1 parts by volume).

Workup

  1. extractionFor extraction, 200 ml of dichloromethane and 100 ml of water
  2. additionare added
  3. customThe organic layer is dried
  4. filtrationfiltered with suction
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a236a81f3ab14516a58e6d1275eaece3
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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