2-Bromothiazole → Thiazole, 2-(phenylthio)-

HRID 507602

Reaktionsgleichung

Reaktionsgleichung von HRID 507602
[C:1]1([S-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].Br[C:10]1[S:11][CH:12]=[CH:13][N:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([S:7][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 764302-BromothiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4110039Sodium benzenethiolate

Produkt 1

HCID 606073Thiazole, 2-(phenylthio)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of sodium thiophenolate (0.61 g, 4.62 mmol) and 2-bromothiazole (0.38 mL, 4.2 mmol) in 20 mL of toluene was treated with 0.19 g (0.21 mmol) of Pd2dba3 and 0.12 g (0.21 mmol) of Xantphos and heated at reflux for 10 min. The crude solution was concentrated onto 5 g of silica gel and then purified by flash chromatography to give the title compound. MS (M+H)+ 194.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 10 min
  3. concentrationThe crude solution was concentrated onto 5 g of silica gel
  4. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f4267e351f8b497abbac57e4cfc78fa0
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786132B2

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