626-87-9

clear colorless to light yellow-brown liquid

1,4-Dibromopentane is used in the preparation of pharaoh ant trail pheromone stereoisomer, indolizidine alkaloid. It is also involved in the preparation 1,2-dimethyl-1-phenylcyclopentane and boc-L-2-amino-6-bromoheptanoic acid.

1,4-Dibromopentane is synthesized by ring-opening bromination of 2-methyltetrahydrofuran with hydrobromic acid and sulfuric acid. First, add hydrobromic acid into the reaction pot for cooling, slowly add 2-methyltetrahydrofuran and sulfuric acid in turn under stirring, and finish the addition when the temperature does not exceed 40°C. The temperature was raised to 60°C, reacted for 2h, and then reacted at 80-85°C for 4h. After cooling, the bromide was separated and washed with water until neutral to obtain 1,4-dibromopentane as an oily substance. Yield 92.5%.

Journal of the American Chemical Society, 74, p. 917, 1952 DOI: 10.1021/ja01124a016