1-Bromo-3-chloropropane → HCID 12798089, compound

Participants

Reaction Steps

To a solution of 5-benzyloxyindazole (30 g) in dimethylformamide (150 ml), 50% sodium hydride (6.7 g) was added and the mixture was stirred at room temperature for 10 minutes. The solution was then added dropwise to 150 ml of dimethylformamide containing 1-bromo-3-chloropropane (30 g) while cooling with ice, and, after stirring at room temperature for 30 minutes, the mixture was extracted with benzene. The extract was washed with water, dried over anhydrous sodium sulfate, and distilled to remove the solvent used. The residue was chromatographed with a column filled with silica gel to give 16 g of 1-(3'-chloropropyl)-5-benzyloxyindazole (m. p. 65°-66° C.) and 4.5 g of 2-(3'-chloropropyl)-5-benzyloxyindazole (m.p. 97°-98° C.).

Provenance & Evidence