Houps sorry
I have posted the wrong reference
The true ref was J org chem vol 50, 8, 1985, 1334-1337!!
In it you will find that the authors has got a 83% yield with acetonitrile and 2-bromo-1,4-dmb
And not I haven't synth it at all, I was searching for a new way to 2,5-diMeo-thiophenol through 2-amino-1,4-dmb and potassium xanthate (I have a ref that say 2,5-diMeo-thiophenol was prepared in 48% yield from 2-amino-1,4-dmb, I will post it soon)
The ref I gave was from the same authors but not the same compound...
Another ref say a similar reaction may bee done from KOt-Bu in toluene (J org chem vol 66,4,2001,1403-1412), this paper describe the synthesis of various amine from benzyne intermediate generated from substituted chloro-benzene, I think that if we use the acetonitrile instead ot the amine the benzyne will react the same and give the phenylacetonitrile:
Synthesis of N-Aryl-2,3-dihydroindoles ans N arylindoles:Starting from commercially available halostyrene (2-chlorostyrene, 3-chlorostyrene, 2,6-dichlorostyrene) various 2,3-dihydroindoles were obtained in the presence of KOt-Bu in toluene at 135°C. Since KOt-Bu is a precatalyst for the hydroamination reaction and a mediator for the aryne-amination reaction, stoichiometric amounts of base have to be used in order to obtain full conversion. In general 3 equiv of KOt-Bu were applied in these reactions; however, the amount of base could be reduced to 1,5 equ. (relative to the aryl chloride) without significantly decreasing the yield. Electron withdrawing (F,CF3,Ph) as well as electron-donating (OCH3) substituents on the aniline. Despite possible side reactions to give alternative aryne intermediates, 3-chlorostyrene reacts with 4-fluoroaniline to yield the substituted 2,3-dihydroindole in a similar yield (50 vs 54%) to 2-chlorostyrene.
(...)
Attempts to react alpha or beta-methyl-2-chlorostyren with aniline in the presence of stoichiometric amounts of bKOt-Bu do not result in the corresponding 2- and 3-substituted 2,3-dihydroindoles. In this case aryne generation as a first reaction step is favored compared to olefin hydroamination. The resulting3-substituted anilines are unable to undergo intramolecular cyclisation via hydroamination.
Well the KOt-Bu in toluene form an aryne derivative with halo-compound, this aryne can be reacted with acetonitrile in the same fashion and you got the phenylacetonitrile.
But wath's wrong with amonia/K-Na or Li, the texas farmers use it to get meth so I think it's not that bad if you are cautious and don't spill it on yourself, just do it like a ghetto birch and all will be fine, thats a nice and rapid proc for 2CH, and you have got greater yield than all the others method afaik. Just reduce the nitrile with Cobalt/NaBH4 or Ni-Raney/hydrazine(which can be synthetised OTC).
It's hardcore chemistry but it's doable and a great proc from easy to get chemicals...
Speak about 2C-B for the Masses