[Woodwardt84]

This will be my first post here 
Im having big troubles in reducing 4-Bromo-2-Butoxybenzonitrile to the benzylamine. I have tried  to use LiAlH4, NaBH4/AlCl3, Dibal-H 2 eqv, NiCl2/NiBH4, LiBH4. The NaBH4/AlCl3 has given poor yields of 35 %. The others have not given the reducted product…Why the difficulty of reducing the nitrile group? If you have some experiences in this reduction or any advise, please tell me!!   Im about to test the (iPr)2N-BH2, but maybe also Raney Nickel or Nickel Boride will do the reduction? Read that maybe electrochimicall reduction of Benzonitrile could work as well? Red-Al? Or Pd hydrogenation? Please tell me if you have some experience in this. I was sure that DIbal or liAlH4 would work but now I have lost all kind of hope almous!
Kim

Forgive my poor english

[opsomath]

Have you considered reductive amination of the aldehyde?

[discodermolide]

This will be my first post here 
Im having big troubles in reducing 4-Bromo-2-Butoxybenzonitrile to the benzylamine. I have tried  to use LiAlH4, NaBH4/AlCl3, Dibal-H 2 eqv, NiCl2/NiBH4, LiBH4. The NaBH4/AlCl3 has given poor yields of 35 %. The others have not given the reducted product…Why the difficulty of reducing the nitrile group? If you have some experiences in this reduction or any advise, please tell me!!   Im about to test the (iPr)2N-BH2, but maybe also Raney Nickel or Nickel Boride will do the reduction? Read that maybe electrochimicall reduction of Benzonitrile could work as well? Red-Al? Or Pd hydrogenation? Please tell me if you have some experience in this. I was sure that DIbal or liAlH4 would work but now I have lost all kind of hope almous!
Kim

Forgive my poor english

Try Raney Nickel in ethanol containing ammonia at normal pressure and temperature.
You may expect some de-bromination.

[Woodwardt84]

Thanks

I have considered the reductive amination from the aldehyde when trying to get the aldehyde from the benzonitrile with dibal (1eqv) was not succesfule either. To  Do the benzaldehyde by another synthesis route will probably take to long time.

Raney nickel i ammonia? Do you have any reference?

[discodermolide]

Thanks

I have considered the reductive amination from the aldehyde when trying to get the aldehyde from the benzonitrile with dibal (1eqv) was not succesfule either. To  Do the benzaldehyde by another synthesis route will probably take to long time.

Raney nickel i ammonia? Do you have any reference?

Look in Houben-Wehyl, the hydrogenation volume. This is a standard procedure.
The presence of ammonia prevents the formation of secondary amines during the hydrogenation.