Iodine → 1-Benzenesulfonyl-2-(3-bromo-phenyl)-aziridine

HRID 560088Notes

Reaction equation

HRID 560088 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:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[CH2:20]>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.O>[C:4]1([S:7]([N:10]2[CH2:20][CH:19]2[C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([Br:15])[CH:17]=2)(=[O:9])=[O:8])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 807IodineHCID 748703-BromostyreneHCID 4347343Chloramine B

Product 1

HCID 866371721-Benzenesulfonyl-2-(3-bromo-phenyl)-aziridineYield 67.6%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred suspension of chloramine B (CAS [127-52-6], 2.97 g), iodine (0.353 g) and trioctylmethylammoniumchloride (Aliquat 336, 0.562 g) in water (40 mL) under argon was added 3-bromostyrene (5.09 g). The mixture was stirred for 2 h at room temperature and subsequently extracted with ethyl acetate. The org. phase was washed with water, dried (MgSO4), filtered and concentrated. The product was purified using column chromatography (SiO2, cyclohexane/ethyl acetate 1:0=>4:1) to give 1-benzenesulfonyl-2-(3-bromo-phenyl)-aziridine (3.18 g) as a light brown oil.

Workup

  1. extractionsubsequently extracted with ethyl acetate
  2. washphase was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified

Sources & evidence

ORD record
ord-df790f8700a248c3bbbfd01d087ff1a5
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

Loading…