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Synthesis of 4-Fluoroamphetamine

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Rhodium:
I cannot seem to find any good references on the preparation of 4-fluorophenyl-2-nitropropene, is there anyone out there who could help me with a literature search?
The only ref on 4-fluorophenethylamines I can find is an article which starts with 4-fluorophenylmagnesium bromide, reacts this with ethylene oxide, brominates the resulting alcohol, and reacts the phenethylbromide with alcoholic NH3 in a bomb. I don't think that's a good route.

LAH is able to remove aromatic halogens, is this true for fluorine too? Does Red-Al have the same disadvantage?

See http://rhodium.lycaeum.org/pharmacology/pfa.txt for some info on 4-fluoro-amphetamine.




http://rhodium.lycaeum.org

Osmium:
As far as I know LAH will leave the fluorine intact.

The only fluorination reaction I can think of right now is the thermal decomosition of diazonium fluoroborates. Very ugly, very toxic, very corrosive reaction.

obituary:
surely, obit is missing something, but would sandmeyer work here?

Rhodium:
4-fluorobenzaldehyde is cheap, so that is a good starting material. But EDDA is a lousy condensation catalyst for this nitropropene, so I hoped that you had better suggestions.

http://rhodium.lycaeum.org

Lilienthal:
Maybe it's only a problem of their crystallization, not of their yield. Sometimes fluorinated compounds behave a bit strange. If I remember correctly it should be possible to use LiAlH4. For dehalogenation you usually need drastic conditions compared to nitropropene reduction.

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