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(2-Bromophenyl)diphenylphosphine

(2-Bromophenyl)diphenylphosphine is an organophosphorus compound with the formula (CHBr)P(CH). It is a white crystalline solid that is soluble in nonpolar organic solvents. The compound is used as a precursor to the 2-lithiated derivative of triphenylphosphine, which in turn is a precursor to other phosphine ligands.

Preparation

The compound has been prepared by several methods. An efficient route is the coupling reaction of diphenylphosphine and 2-bromoiodobenzene, which is catalyzed by palladium complexes (Ph = CH):

CHBr(I) + HPPh + EtN → PhP(CHBr) + [EtNH]I

The compound is isomorphous with (2-tolyl)diphenylphosphine.

Lithiation with butyl lithium gives o-lithiated triphenylphosphine. The bromide also forms a Grignard reagent. These metallated phosphines are versatile reagents.

BrC<sub>6</sub>H<sub>4</sub>PPh<sub>2</sub> + Mg → BrMgC<sub>6</sub>H<sub>4</sub>PPh<sub>2</sub>
2 BrMgC<sub>6</sub>H<sub>4</sub>PPh<sub>2</sub> + PhPCl<sub>2</sub> → PhP[C<sub>6</sub>H<sub>4</sub>PPh<sub>2</sub>]<sub>2</sub> + 2 MgClBr

References