Chlorodiphenylphosphine → Methyl 2-diphenylphosphino-1-naphthoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 66.6 g (0.195 mol) of 1-carbomethoxy-2-(trifluoromethylsulfonyloxy)naphthalene in 450 ml DMF were added, under a nitrogen atmosphere, 3.65 g NiCl2 (dppe) (6.9 mmol) and 35 ml ClPPh2 (0.195 mol). The reaction mixture was cooled in an ice-water bath and 15 g zinc (20% excess) was added portionwise at 8°-15° C. The mixture was then heated to 108° C. for 2 hours, cooled to 50° C., filtered through silica and washed with three 20 ml portions of methanol. The filtrate was concentrated under vacuum to half of its original volume and allowed to crystallize at 0°-4° C. The product was collected and washed with methanol. Further concentration of the filtrate caused additional material to crystallize. The total yield of the title compound was 66.3 g (92%).

Provenance & Evidence