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Methyltriphenylphosphonium bromide

Methyltriphenylphosphonium bromide is the organophosphorus compound with the formula [(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PCH<sub>3</sub>]Br. It is the bromide salt of a phosphonium cation. It is a white salt that is soluble in polar organic solvents.

Synthesis and reactions

Methyltriphenylphosphonium bromide is produced by treating triphenylphosphine with methyl bromide:

Ph<sub>3</sub>P + CH<sub>3</sub>Br → Ph<sub>3</sub>PCH<sub>3</sub>Br

Methyltriphenylphosphonium bromide is the principal precursor to methylenetriphenylphosphorane, a useful methylenating reagent. This conversion is achieved by treating methyltriphenylphosphonium bromide with strong base.

Ph<sub>3</sub>PCH<sub>3</sub>Br + BuLi → Ph<sub>3</sub>PCH<sub>2</sub> + LiBr + BuH

References