2-(4-Bromophenyl)thiazole
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2-(4-Bromophenyl)thiazole
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CAS No:
27149-27-5
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Formula:
C9H6BrNS
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Chemical Name:
2-(4-Bromophenyl)thiazole
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Synonyms:
Thiazole,2-(4-bromophenyl)-;Thiazole,2-(p-bromophenyl)-;2-(4-Bromophenyl)thiazole;2-(4-Bromophenyl)-1,3-thiazole
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CAS No:
2-(4-Bromophenyl)thiazole Use and Manufacturing
A flask which in 2-bromothiazole (16.4 g) and 50 ml of THF solution were put was cooled in an iced bath, and then 55 ml of a THF solution of 2 M isopropylmagnesium chloride was added dropwise there to under in a in nitrogen atmosphere while stirring the solution. After dropewise addition the rection mixture was stirred for 1 hour, and then a zinc chloride-tetramethylethylenediamine complex (30.3 g) was added. the resuting mixture was stirring for 1 hour at room temperature, and then 1-bromo-4-iodobenzene (28.3 g) and Pd(PPh3)4 (3.5 g) were added and then heated and stirred for 1.5 hours at reflux temperature. After cooling the reaction solution to room temperature, to remove the metal ions of the catalyst, a solution prepared by dissolving the compound ethylenediamine Inc. acid, use the sodium salt dihydrate equivalent to approximately 2-fold molar with respect to the objective to the appropriate amount of water (after and it stirred to fall abbreviated) EDTA · 4Na in an aqueous solution. Then, after removing also separated by adding toluene, and the solvent was distilled off under reduced pressure to the solution, and purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 50/1 (volume ratio)) to give 2-(4-bromophenyl)thiazole (18.3g).A flask in which 2, 2 '-(2-phenylanthracene-9, 10-diyl)bis(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane)(3.5 g) See the sythesis method described in Japanese Patent Publication No. 2008-247895, 2- (4-bromophenyl)thiazole (3.7 g), tripotassium phosphate (5.9 g), Pd(PPh3)4 (0.2g), 1, 2, 4-trimethylbenzene (20 ml) flask and water (2 ml) was stirred into the heated 7.5 hours at reflux temperature. The reaction mixture was cooled to room temperature and was separated by adding water and toluene. The solvent was distilled off under reduced pressure, purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 50/1 (volume ratio)) was purified by. Recrystallization of the solid obtained by distilling off the solvent under reduced pressure from chlorobenzene, compound (1-3): 2, 2 '-((2-phenylanthracene-9, 10-diyl)bis(4, 1-phenylene))dithiazole (1.9 g).A flask which in 2-bromothiazole (16.4 g) and 50 ml of THF solution were put was cooled in an iced bath, and then 55 ml of a THF solution of 2 M isopropylmagnesium chloride was added dropwise there to under in a in nitrogen atmosphere while stirring the solution. After dropewise addition the rection mixture was stirred for 1 hour, and then a zinc chloride-tetramethylethylenediamine complex (30.3 g) was added. the resuting mixture was stirring for 1 hour at room temperature, and then 1-bromo-4-iodobenzene (28.3 g) and Pd(PPh3)4 (3.5 g) were added and then heated and stirred for 1.5 hours at reflux temperature. After cooling the reaction solution to room temperature, to remove the metal ions of the catalyst, a solution prepared by dissolving the compound ethylenediamine Inc. acid, use the sodium salt dihydrate equivalent to approximately 2-fold molar with respect to the objective to the appropriate amount of water (after and it stirred to fall abbreviated) EDTA · 4Na in an aqueous solution. Then, after removing also separated by adding toluene, and the solvent was distilled off under reduced pressure to the solution, and purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 50/1 (volume ratio)) to give