Rh,
Are you looking for references to 4-fluoroamphetamine proper, or just any 4-fluoroamphetamine?
LAH definately has the potential to chew of aromatic bromides and iodides, but chlorides and fluorides are less susceptable. If you're still worried, you can use you LAH to prepare alane, which will leave any halide alone. Shulgin uses this technique anywhere where a the Lewis acidity of LAH causes interference with electron-pair rich substituents in order to obtain better yields (e.g. - several 2C-T's.)
2LiAlH
4 + H
2SO
4 -> 2 AlH
3 + Li
2SO
4 + 2 H
2As would be expected, lower temps are good (O C is about right, if I remember.)
Here are a few references citing fluorinated nitrostyrenes being reduced to phenethylamines. The second one in the list explicitly includes 4-fluoroamphetamine using LAH, though the yields are not so impressive (52%.)
J.Med.Chem.; EN; 11; 4; 1968; 814-819;
J.Med.Chem.; EN; 33; 7; 1990; 2015-2019;
J.Med.Chem.; EN; 35; 16; 1992; 2970-2978;
J.Med.Chem.; EN; 33; 9; 1990; 2408-2412;
J.Med.Chem.; EN; 29; 11; 1986; 2250-2256;
Synth.Commun.; EN; 24; 3; 1994; 417-426;
Farmaco Ed.Sci.; EN; 43; 1; 1988; 49-60;
J.Med.Chem.; EN; 38; 25; 1995; 4929-4936;
J.Fluorine Chem.; EN; 74; 2; 1995; 303-306;
Med.Chem.Res.; EN; 6; 5; 1996; 318 - 332;
J.Med.Chem.; EN; 39; 21; 1996; 4261-4274;
Eur.J.Med.Chem.Chim.Ther.; EN; 34; 2; 1999; 137 - 152;
Alternatively, if you're still paranoid that LAH will do bad things to your fluoride, you can use borane/diborane complexes as your hydride source. BH
3*THF is cheap and reasonably available, and is especially mild in this regard. The yields are generally good using that too.
So now that I've answered the question, tell me what's interesting about 4-fluoroamphetamine? Do you know something the rest of us don't?
![Wink ;)](https://thevespiary.org/talk/Smileys/default/wink.gif)