2-Bromothiazole → HCID 23510389, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, a solution of 2-bromothiazole (2.00 g) in Et2O (38 mL) was cooled to −78° C., and thereto was added a 1.5N solution of n-BuLi in hexane (8.5 mL), and the mixture was stirred at −78° C. for 30 minutes. To the mixture was added a 1.0N solution of ZnCl2 in Et2O (12.2 mL), and the mixture was stirred at −78° C. for 10 minutes, and stirred at room temperature for 30 minutes. To the mixture were added successively Pd(PPh3)4 (704 mg) and ethyl 4-iodobenzoate (2.26 g), and the mixture was stirred at 66° C. for 1 hour. To the mixture was added a 1.0N solution of ZnCl2 in Et2O (12.2 mL), and the mixture was stirred at 66° C. for 2 hours. To the mixture was added THF (60 mL), and the mixture was stirred at 66° C. for 2.5 hours. To the mixture were added a 0.18N aqueous solution of ethylene-diaminetetraacetic acid disodium salt dihydrate (300 mL), and sodium hydrogen carbonate until the pH value of the mixture became pH=8. The mixture was extracted with ethyl acetate, washed with an aqueous NaHSO3 solution, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=12.5/1) to give ethyl 4-(1,3-thiazol-2-yl)benzoate (1.35 g, 71%).

Provenance & Evidence