Hydrochloric Acid → HCID 15338398, compound

Participants

Reaction Conditions

Reaction Steps

24.3 g (33.6 ml, 0.240 mol) diisopropylamine was dissolved in 100 ml THF while stirring in a nitrogen atmosphere and it was added dropwise at -50° C. to 100 ml (0.240 mol) of a 2.40 M solution of butyllithium in hexane. It was allowed to reach -10° C. for 10 minutes, a solution of 15.5 g (0.120 mol) dichloroacetic acid in 20 ml THF was then added dropwise at -75° C., it was stirred for 25 minutes at -75° C. and subsequently 93.5 g (55.0 ml, 0.41 mol) 1,5-dibromopentane in 50 ml THF was added in such a way that the temperature increased to -40° C. After 2.5 hours at -40° C. it was hydrolyzed with 10 ml 6 N HCl and the precipitate that formed was dissolved with 20 ml water. The organic phase was washed twice with a small amount of water, dried over magnesium sulfate and the solvent was removed in a vacuum. Flash chromatography of the residue on silica gel (mobile solvent: ethyl acetate/heptane 1:10) yielded 19.5 g (59%) 7-bromo-2,2-dichloroheptanoic acid 5 as a colourless oil.

Provenance & Evidence