Phenylmagnesium Bromide is one of numerous organomagnesium Grignard reagents manufactured by American Elements under the trade name AE Organometallics™. Organometallics are useful reagents, catalysts, and precursor materials with applications in thin film deposition, industrial chemistry, pharmaceuticals, LED manufacturing, and others. American Elements supplies organometallic compounds in most volumes including bulk quantities and also can produce materials to customer specifications. Please request a quote above for more information on pricing and lead time.
Decacarbonyldimanganese has been prepared by reacting carbon monoxide at 200 atm at room temperature for 15–17 h with a mixture of magnesium powder, manganese iodide, copper and copper iodide suspended in diethyl ether <54JA3831>, by the action of phenylmagnesium bromide or chloride and carbon monoxide at 30 atm on anhydrous MnCl2 in diethyl ether at −20 to 30 °C <58USP2822247>, and by reducing manganese(II) salts with sodium benzophenone ketyl in THF, carbonylating the resulting mixture with carbon monoxide at 200–700 atm and 65–200 °C and hydrolysing and steam distilling the Mn2(CO)10 from the resulting mixture <58JA6167>. The reduction of an anhydrous manganese(II) salt with a trialkylaluminum compound dissolved in an ether or benzene in the presence of carbon monoxide under pressure results in a 60% yield of the required compound <58IZV100, 60JA1325, 65IC293>.
Tacke and Becker synthesized the hydroxymethylgermane (14) from tetrachlorogermane in 32% overall yield <88JOM(354)147> in a four-step sequence that has clear potential for the preparation of a series of variously substituted products (Scheme 4). Yields in the diphenyl series, generated using phenylmagnesium bromide in the second step, were uniformly 15–20% higher.
Diphenylprolinol was first synthesised in 1933 from proline ethyl ester by reaction with phenylmagnesium bromide. However, it was not until 1961, when racemic diphenylprolinol was synthesised using this method for potential clinical applications, that this compound was shown to have central stimulant activity when administered parentally to rats [14]. A few years later, the reduction of diphenylprolinol using hydriodic acid was reported in the patent literature [16] for the production of (S)-2-diphenylmethylpyrrolidine as a potential central stimulant.

Interestingly, pipradrol, diphenylprolinol and 2-(diphenylmethyl)pyrrolidine later found use as chiral organic catalysts [37,42–44], which subsequently led to an explosion of research on organocatalysts [44]. Kanth reported a convenient synthesis of diphenylprolinol from (S)-proline using ethyl chloroformate to simultaneously produce the (S)-proline ethyl ester with an N-protecting group. This intermediate was then reacted with phenylmagnesium bromide to produce a cyclic carbamate which was then hydrolyzed with potassium hydroxide (Fig. 10.7) [45]. A nitrogen-protecting group has also been utilised for the synthesis of diphenylprolinol from pyrrolidine and benzophenone [41]. The chiral properties of 2-(diphenylmethyl)pyrrolidine have also been exploited in analytical chemistry as a chiral solvating agent for the determination of enantiomeric composition of chiral carboxylic acids by NMR analysis [46]. For this application, Bailey modified the method of Kanth by hydrogenating the cyclic carbamate to produce 2-diphenylmethylpyrrolidine