p-Tolyl methyl sulfone → 4-(Methylsulfonyl)benzyl Bromide

HRID 747386

Reaktionsgleichung

Reaktionsgleichung von HRID 747386
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([CH3:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:10][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH2:11][Br:12])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Komponenten

4

Edukt 2

HCID 18521p-Tolyl methyl sulfoneHCID 67184N-bromobutanimide

Produkt 1

HCID 27335814-(Methylsulfonyl)benzyl BromideAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Methyl p-tolyl sulfone (24 g, 0.14 mol) in 550 ml CCl4 was heated to reflux temperature, N-bromosuccinimide (17.8 g, 0.14 mol) was added in portions and the mixture was refluxed for 3 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated to yield 4-methanesulfonylbenzyl bromide as a crystalline solid (32.9 g), 1H-NMR (CDCl3) δ 8.05 (d, 2H), 7.70 (d, 2H), 4.45 (s, 2H), 3.09 (s, 3H). To the crude product in water (200 ml) were added sodium sulfite (33.2 g, 264 mmol) and tetrabutylammonium bromide (0.41 g, 1.64 mmol), and the mixture was refluxed for 2 h. After cooling to room temperature the solution was extracted with ethyl acetate, the aqueous phase was then concentrated to half the volume and cooled. The precipitate was filtered off and dried under vacuum at 70° C. to yield sodium 4-methanesulfonyl-benzylsulfonate (33.3 g, quant.).

Aufarbeitung

  1. additionwas added in portions
  2. temperaturethe mixture was refluxed for 3 h
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e689fc2b7d38400f92aa962ebb42ddc4
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396846B2

Verknüpfte Notizen

Wird geladen…