Uses
n-Butyltriphenylphosphonium Bromide is used in the synthesis of inhibitors of tubulin polymerization thus expressing antimitotic and antitubulin properties. Also used in the synthesis of 3-phenylpropanoic acids as peroxisome proliferator-activated receptor dual agonists affecting the mitochondrial carnitine system.
Uses
Reactant for:
Free radical 5-exo-dig cyclization
Intramolecular hydroacylalkoxylation
Wittig reactions for stereoselective synthesis of alkenes
Dimerization of α-olefins
Alkylidenation of hydrazides for synthesis of indoles
Tandem cyclization and 1,2-thiolate shift of nitrogen ylides
Synthesis
Under nitrogen protection, 280 g of bromobutane and 696 g of triphenylphosphine were added to a 2 L four-neck flask dissolved in 500 mL of xylene. The reaction mixture was heated to reflux temperature with continuous stirring for 6 hours. After completion of the reaction, the system was cooled to room temperature, the precipitated white crystals were collected by filtration and washed with xylene. After drying, 797 g of butyltriphenylphosphonium bromide was obtained as a white solid in 97.7% yield.
References
[1] Patent: JP6136589, 2017, B2. Location in patent: Paragraph 0102-0104
[2] Acta Chimica Hungarica, 1987, vol. 124, # 5, p. 737 - 748
[3] Journal of Fluorine Chemistry, 2002, vol. 113, # 2, p. 177 - 183
[4] Pharmazie, 1999, vol. 54, # 1, p. 26 - 30
[5] Synthetic Communications, 1981, vol. 11, # 2, p. 125 - 132
