5-Phenylthiazole → 5-Bromo-2-chloro-1-(5-phenyl-2-thiazolylmethyl)benzene

HRID 221109

Reaktionsgleichung

Reaktionsgleichung von HRID 221109
[C:1]1([C:7]2[S:11][CH:10]=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:21])=[C:17]([CH:20]=1)[CH:18]=O>>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:21])=[C:17]([CH2:18][C:10]2[S:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][N:9]=2)[CH:20]=1

Komponenten

3

Edukt 2

HCID 5952095-PhenylthiazoleHCID 106089255-Bromo-2-chlorobenzaldehyde

Produkt 1

HCID 666083225-Bromo-2-chloro-1-(5-phenyl-2-thiazolylmethyl)benzene

Versuchsvorschrift

A solution of thiazole (10.0 g), iodobenzene (2.63 ml), tetrakis(triphenylphosphine)palladium (0) (1.36 g) and potassium acetate (3.46 g) in N,N-dimethylacetamide (100 ml) was stirred under heating at 100° C. overnight. The solvent was evaporated under reduced pressure, and added to the residue was ethyl acetate. The mixture was washed successively with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10) to give 5-phenylthiazole (1.50 g) as a pale yellow solid. APCI-Mass m/Z 162 (M+H). (2) The above 5-phenylthiazole and 5-bromo-2-chlorobenzaldehyde obtained in Reference Example 16-(1) were treated in a manner similar to Reference Example 100 to give 5-bromo-2-chloro-1-(5-phenyl-2-thiazolylmethyl)benzene as a yellow solid. APCI-Mass m/Z 364/366 (M+H).

Aufarbeitung

  1. additionwere treated in a manner similar to Reference Example 100

Quellen und Nachweise

ORD-Eintrag
ord-10704897e8b64bc8937acb01f3d818ba
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202984B2

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