Tributylstannane → 1-Bromo-2-(2,2,2-trifluoroethyl)benzene

HRID 1094811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094811
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8](OC(N1C=CN=C1)=S)[C:9]([F:12])([F:11])[F:10].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([F:10])([F:11])[F:12]

Komponenten

4

Edukt 2

HCID 5948TributylstannaneHCID 57582364Imidazole-1-carbothioic acid O-[1-(2-bromophenyl)-2,2,2-trifluoroethyl]-ester

Produkt 1

HCID 457904731-Bromo-2-(2,2,2-trifluoroethyl)benzeneAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of imidazole-1-carbothioic acid O-[1-(2-bromophenyl)-2,2,2-trifluoroethyl]-ester (Preparation 56, 27.0 g, 73.8 mmol) in toluene (400 ml) was heated at reflux and treated with tri-n-butyltin hydride in three portions: 22 g (75.6 mmol) at first, an additional 10 g (34.4 mmol) after 30 min, and finally 11 g (37.8 mmol) 30 min later. After the addition, the mixture was heated at reflux for another 30 min. The reaction mixture was cooled then the product was distilled at 25 Pa, 60-100° C. to afford the title compound as a colourless oil (17.0 g, 59%).

Aufarbeitung

  1. temperatureat reflux
  2. customfinally 11 g (37.8 mmol) 30 min
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux for another 30 min
  6. temperatureThe reaction mixture was cooled
  7. distillationthe product was distilled at 25 Pa, 60-100° C.

Quellen und Nachweise

ORD-Eintrag
ord-7b92846416f54a358a6c43e185f2430a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134007B2

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