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

HRID 560088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 560088
[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

Komponenten

6

Edukt 3

HCID 807IodineHCID 748703-BromostyreneHCID 4347343Chloramine B

Produkt 1

HCID 866371721-Benzenesulfonyl-2-(3-bromo-phenyl)-aziridineAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-df790f8700a248c3bbbfd01d087ff1a5
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063088B2

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