Potassium Carbonate → 2-(4-Methoxy-phenyl)-thiazole

HRID 1669507

Reaktionsgleichung

Reaktionsgleichung von HRID 1669507
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 201262(4-Methoxyphenyl)boronic acid

Produkt 1

HCID 112984492-(4-Methoxy-phenyl)-thiazoleAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromothiazole (2.0 g, 12.2 mmol), (4-methoxyphenyl)boronic acid (1.9 g, 12.8 mmol), K2CO3 (5.0 g, 36.5 mmol) and (Ph3P)4Pd (0.7 g, 0.61 mmol) in dioxane (40 mL) was refluxed for 16 h. After the solids were filtered off, the filtrate was concentrated in vacuo. The residue was purified by a column chromatography on silica gel to yield the title compound (1.1 g, 50%). 1HNMR (400 MHz, CDCl3) δ 3.86 (s, 3H), 6.96 (d, J=8.8 Hz, 2H), 7.25 (d, J=3.2 Hz, 1H), 7.81 (d, J=3.2 Hz, 1H), 7.90 (d, J=8.8 Hz, 2H), MS m/z 192 (M+1).

Aufarbeitung

  1. temperaturewas refluxed for 16 h
  2. filtrationAfter the solids were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7dcb3fc5b6774c8c97a5eb1a7a548592
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989480B2

Verknüpfte Notizen

Wird geladen…