TRI-P-TOLYLPHOSPHINE synthesis

7synthesis methods

Product Name:TRI-P-TOLYLPHOSPHINE
CAS Number:1038-95-5
Molecular formula:C21H21P
Molecular Weight:304.37

Tri-p-tolylphosphine can be used as a catalyst ligand for coupling reaction; in terms of materials, it is used for the synthesis of flame retardants. Its synthesis method is as follows: using p-bromotoluene and magnesium scraps as raw materials, tetrahydrofuran as a solvent, react with iodine as an initiator, to give p-methylphenylmagnesium bromide. Tri-p-tolylphosphine can be synthesized by a nucleophilic reaction of P-methylphenylmagnesium chloride and phosphorus trichloride.

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1038-95-5
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Yield:1038-95-5 91%

Reaction Conditions:

with chloro-trimethyl-silane;magnesium at 20; for 4 h;

Steps:

A typical procedure for the reduction of 2a

General procedure: To a mixture of Mg powder (8 mmol, 4 mol equiv), Me3SiCl (6 mmol, 3 mol equiv), and DMI (8 mL) was added 2a (2 mmol), and the whole mixture was stirred for 2 h at room temperature. To the reaction mixture was added satd aq (NH4)2CO3, and the mixture was extracted with Et2O (10 mL 3). The combined organic layers were washed with satd aq NaCl, dried over Na2SO4, and concentrated under reduced pressure. The resultant was analyzed by 31P NMR to find that 1a and 2a were obtained in 97:3 ratio. The desired 1a was obtained in 96% yield after purification by silica gel column chromatography (hexane/AcOEt = 5:1) (Table 1, entry 1).

References:

Kuroboshi, Manabu;Kita, Toshihito;Aono, Asuka;Katagiri, Toshimasa;Kikuchi, Seiya;Yamane, Syoko;Kawakubo, Hiromu;Tanaka, Hideo [Tetrahedron Letters,2015,vol. 56,# 7,p. 918 - 920]