Hydrochloric Acid → 9,9,10,10-Tetrafluoro-2,7-dihexyl-9,10-dihydrophenanthrene

Participants

Reaction Conditions

Reaction Steps

4.1 g of 9,9,10,10-tetrafluoro-2,7-dibromo-9,10-dihydrophenanthrene are dissolved in 250 ml of THF and the solution is cooled to 0° C. 120 mg of 1,3-bis(diphenylphosphine)propanenickel(lI) chloride are added, and, at 0° C., 50 mmol of hexylmagnesium bromide in 100 ml of THF are added dropwise. Stirring is continued for 4 hours, and then for a further 18 hours at 50° C. The mixture is acidified with 1N HCl, the aqueous phase is saturated with NaCl and the phases are separated. The aqueous phase is subsequently subjected to extraction a number of times with tert-butyl methyl ether. The crude product is purified by chromatography on silica gel. This gives 3.45 g of 9,9,10,10-tetrafluoro-2,7-dihexyl-9,10-dihydrophenanthrene.

Provenance & Evidence