Sulfuric Acid → 11-bromoundec-10-ynoic Acid

Participants

Reaction Steps

To a solution of 36.45 g (200 mmol) of 10-undecynoic acid in 200 ml 1N NaOH at 0° C. was added a solution of alkaline sodium hypobromite dropwise over 30 minutes, maintaining the temperature below 5° C. (the hypobromite solution was prepared by the dropwise addition of 35.16 g (220 mmol) of bromine to 55 ml of 20N NaOH at 0°-5° C.). The mixture was stirred four hours at 0°-5° C., and was then acidified to pH 1 with 9M H2SO4. The solution was extracted with three 150 ml portions of ether. The combined extracts were dried (Na2SO4) and evaporated yielding 50.159 (96% crude) of a pale yellow solid. This was used without further purification.

Provenance & Evidence