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

HRID 221109Notes

Reaction equation

HRID 221109 reaction equation
[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

Participants

3

Reactant 2

HCID 5952095-PhenylthiazoleHCID 106089255-Bromo-2-chlorobenzaldehyde

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-10704897e8b64bc8937acb01f3d818ba
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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