Bromine → 4'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamide

HRID 36298

Reaktionsgleichung

Reaktionsgleichung von HRID 36298
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15](=[O:22])(=[O:21])[NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:23]Br>C(Cl)(Cl)(Cl)Cl.[W]>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15](=[O:22])(=[O:21])[NH:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:5]=[CH:6][C:7]=1[CH2:8][Br:23]

Komponenten

5

Edukt 2

HCID 24408BromineHCID 100874243-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

Produkt 1

HCID 100465214'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamideAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23964TungstenKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

A solution of 1.08 g (3.36 mmol) of 3-fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl (from Step A) in 20 mL of CCl4 was stirred at reflux under irradiation from a 100-watt tungsten lamp as a solution of 3.5 mmol of bromine in approximately 13 mL of CCl4 was added dropwise over 1.5 hour. After being stirred at reflux overnight, the solution was cooled and concentrated. The residue was crystallized from EtOAc-hexane to give 1.10 g of the title compound as an off-white solid, mp 138°-140° C. (estimated purity 87%; contained minor unbrominated and dibrominated contaminants by TLC); mass spectrum (FAB) m/e 400, 402 (M+1)+.

Aufarbeitung

  1. additionwas added dropwise over 1.5 hour
  2. temperatureat reflux overnight
  3. temperaturethe solution was cooled
  4. concentrationconcentrated
  5. customThe residue was crystallized from EtOAc-hexane

Quellen und Nachweise

ORD-Eintrag
ord-44e3ba39eab54a15a4de1eaa21287227
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411980

Verknüpfte Notizen

Wird geladen…