Phosphonium, (5-carboxypentyl)triphenyl-, bromide (1:1)

White Crystalline Solid

A solution of6-bromohexanoic acid (10.00 g, 51.27 mmol) and triphenyl phosphine (14.12 g, 53.83 mmol) in freshly distilled acetonitrile (50 mL) was vigorously stirred and refluxed for 48 hours. The solution was allowed to come to ambient temperature and the Wittig salt was precipitated upon scratching the inside wall of the glass reaction vessel with a spatula. The white solid product was collected, washed with ether and filtered to provide the title compound in 98percent yield (22.87 g): Triphenylphosphine (20 mg, 0.076 mmol) and 6-bromohexanoic acid (14.8 mg, 0.076 mmol) were dissolved in dry toluene (0.2 mL). The reaction mixture was refluxed over 72 hours. The solution was concentrated. The residue was washed consecutively with benzene (3 x 1 mL), hexane (1 mL), and EtA solution of 6-bromohexanoic acid (3.9 g, 20.0 mmol, 1 equiv) in anhydrous acetonitrile (16 mL) was treated with triphenylphosphine (6.3 g, 24.0 mmol, 1.2 equiv) and warmed at reflux for 20 h. The reaction mixture was concentrated and the crude product was purified by column chromatography (SiOGeneral procedure: A mixture of ω-bromocarboxylic acid (1 equiv) and triphenylphosphine (1 equiv) in 300 mL of toluene was refluxed for 48 h under argon. The mixture was allowed to cool at room temperature and concentrated in vacuum. The residue was crystallized from various solvents to give the corresponding phosphonium salt.Bromohexanoic acid (0.600 g, 3.076 mmol) and triphenylphosphine (0.968 g 3.691 mmol) were dissolved in 40 mL of acetonitrile.This reaction was refluxed for 24 h under a NA solution of 6-Bromohexanoic acid (3g, 0.0512 moles) and triphenylphosphine 4.8g, 0.018 moles) in dry acetonitrile (5OmL) was refluxed for 20-24 h and excess solvent was removed under reduced pressure to afford a color less oil which was triturated with dry benzene and wash in succession with dry benzene and ether (3 times each). During the washing procedure the material crystallized drying at reduced pressure afford Wittig salt as a white micro- crystalline powder (3.6g, 55percent yield).A solution of 6-Bromohexanoic acid (3 g, 0.0512 moles) and triphenylphosphine 4.8 g, 0.018 moles) in dry acetonitrile (50 mL) was refluxed for 20-24 h and excess solvent was removed under reduced pressure to afford a color less oil which was triturated with dry benzene and wash in succession with dry benzene and ether (3 times each). During the washing procedure the material crystallized drying at reduced pressure afford Wittig salt as a white micro-crystalline powder (3.6 g, 55percent yield).

(5-Carboxypentyl)(triphenyl)phosphonium bromide is used in medicine and as pharmaceutical intermediate. It is also employed as catalyst.
Reactant for:

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Molecular Weight:457.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:9
Exact Mass:456.08538
Monoisotopic Mass:456.08538
Topological Polar Surface Area:37.3
Heavy Atom Count:28
Complexity:386
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes