GENERAL STEPS: 2-Bromothiazole (16.4 g) was dissolved in 50 ml of THF under nitrogen protection and cooled in an ice bath. 55 ml of 2M isopropylmagnesium chloride solution in THF was slowly added dropwise while stirring. After the dropwise addition was completed, stirring of the reaction mixture was continued for 1 hour. Subsequently, zinc chloride-tetramethylethylenediamine complex (30.3 g) was added and stirred at room temperature for 1 hour. Next, 1-bromo-4-iodobenzene (28.3 g) and Pd(PPh3)4 (3.5 g) were added, heated to reflux temperature and stirred for 1.5 hours. After completion of the reaction, it was cooled to room temperature. To remove metal ions from the catalyst, about 2 times the molar amount of ethylenediaminetetraacetic acid disodium salt (EDTA-4Na) aqueous solution was added. Subsequently, the organic phase was separated by extraction with toluene and the solvent was removed by distillation under reduced pressure. Finally, the target product 2-(4-bromophenyl)thiazole (18.3 g) was purified by silica gel column chromatography (eluent: toluene/ethyl acetate = 50/1, v/v).
