Iodine → 1-Benzenesulfonyl-2-(4-bromo-phenyl)-aziridine

HRID 560082Notes

Reaction equation

HRID 560082 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([S:7]([N-:10]Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Na+].II.[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH2:21])=[CH:18][CH:17]=1.ClCCl>C(#N)C.O>[C:4]1([S:7]([N:10]2[CH2:21][CH:20]2[C:19]2[CH:22]=[CH:23][C:16]([Br:15])=[CH:17][CH:18]=2)(=[O:9])=[O:8])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 807IodineHCID 6344DichloromethaneHCID 162634-BromostyreneHCID 4347343Chloramine B

Product 1

HCID 468456691-Benzenesulfonyl-2-(4-bromo-phenyl)-aziridineYield 48.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of chloramine B (CAS [127-52-6], 1.35 g) in acetonitrile (18 mL) under argon was added iodine (0.16 g). 4-Bromostyrene (2.41 g) was added and the mixture was stirred for 19 h at room temperature. Dichloromethane (240 mL) and water (120 mL) were added and the mixture was extracted with dichloromethane. The org. phase was washed with water and brine, dried over MgSO4 and K2CO3 and filtered. The filtrate was concentrated and the product was purified using column chromatography (SiO2, cyclohexane/ethyl acetate 95:5=>ethyl acetate) to give 1-benzenesulfonyl-2-(4-bromo-phenyl)-aziridine (1.04 g) as a colorless oil. MS: 340.0 ([M+H]+)

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washphase was washed with water and brine
  3. dry with materialdried over MgSO4 and K2CO3
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe product was purified

Sources & evidence

ORD record
ord-544429e502314da8a3d57eaade455ae0
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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