Methyltriphenylphosphonium bromide is the organophosphorus compound with the formula [(C6H5)3PCH3]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:[1]

Ph3P + CH3Br → Ph3PCH3Br

Methyltriphenylphosphonium bromide is the principal precursor to methylenetriphenylphosphorane, a useful methylenating reagent. This conversion is achieved by treating methyltriphenylphosphonium bromide with strong base.[2]

Ph3PCH3Br + BuLi → Ph3PCH2 + LiBr + BuH

References

  1. ^ Wittig, Georg; Schoellkopf, U. (1960). "Methylenecyclohexane". Organic Syntheses. 40: 66. doi:10.15227/orgsyn.040.0066.
  2. ^ Fitjer, Lutz; Quabeck, Ulrike (1985). "The Wittig Reaction Using Potassium-tert-butoxide High Yield Methylenations of Sterically Hindered Ketones". Synthetic Communications. 15 (10): 855–864. doi:10.1080/00397918508063883.
Allikas: http://en.wikipedia.org/wiki/Methyltriphenylphosphonium_bromide
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