Bromine → HCID 90092744, compound

Participants

Reaction Steps

Sodium acetate (0.26 g, 3.17 mmol) was added to a solution of 2-[5-(dimethoxymethyl)-1H-pyrazol-3-yl]-1,3-thiazole (8b) (714 mg, 3.17 mmol) in chloroform (7.7 mL) and acetic acid (7.7 mL). The mixture was stirred at room temperature for 1 hour. After cooling to 0° C., a solution of bromine (0.155 mL, 3.01 mmol) in acetic acid (1.8 mL) was added dropwise. The reaction mixture was stirred at the same temperature for 40 minutes before being diluted with dichloromethane (10 mL). The mixture was neutralized with 2N sodium hydroxyde to pH 6. The layers were separated and the aqueous layer was extracted with dichloromethane (10 mL). The combined organic layers were dried over sodium sulfate, concentrated in vacuo, and co-evaporated with toluene to provide 2-[4-bromo-5-(dimethoxymethyl)-1H-pyrazol-3-yl]-1,3-thiazole (8c) (900 mg, 2.96 mmol, 93%) which was used without further purification.

Provenance & Evidence