2,7-dibromo-9,9,10,10-tetrafluorophenanthrene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In analogy to Example 1, from 4.1 g of 9,9,10,10-tetrafluoro-2,7-dibromo-phenanthrene and 10 mmol of octylmagnesium bromide. The catalyst used is 0.2 mmol of 1,3-bis(diphenylphosphine)butanenickel(ll) chloride. Chromatography gives 2.4 g of 9,9,10,10-tetrafluoro-2-bromo-7-octyl-9,10-dihydrophenanthrene.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In analogy to Examples 1 and 2, 9,10-difluoro-2,7-dibromophenanthrene and 9,9,10,10-tetrafluoro-2,7-dibromo-9,10-dihydrophenanthrene can be reacted with other Grignard reagents to give symmetrically substituted compounds of the formula (Ia1) and (Ia2). to give symmetrically substituted compounds of the formula (Ia1) and (Ia2)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. for a further 18 hours at 50° C 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