2,2'-Bis(bromomethyl)-1,1'-biphenyl → 2,2'-Bis{di[p-(3-phenylpropyl)phenyl]phosphinomethyl}-1,1-biphenyl

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Reaction Steps

Di[p-(3-phenylpropyl)phenyl]chlorophosphine 1 (6.0 g, 13.1 mmol) was dissolved in 150 ml THF and Li (0.185 g, 26.2 mmol) was chopped directly into the reaction flask under Ar. A deep red solution was resulted in 10 min and all the lithium was consumed in 4 h. The solution was then filtered and 2,2'-dibromomethyl-1,1'-biphenyl (2.23 g, 6.5 mmol) in 20 ml THF was added dropwise with an ice-water bath. The color of the solution was slowly changed to pale yellow. The mixture was stirred for additional 10 h before the solvent was removed by vacuum. 50 ml diethyl ether was added and it was washed with 3×10 ml H2O. The ether phase was dried over MgSO4 and the solvent was then removed by vacuum. The resulting pale yellow viscous oil was purified over silica gel column. 2.3 g (69% yield) of 11 was eluted with Et2O/hexane (1/10), 11 was characterized by 1H, 13C, 31P NMR and Mass spectrometry.

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