hydroxylated 2C-B/I

niobium · Tue Oct 04, 2005 10:32 pm

hello folks.
Niobium here, new name old hand Smile

anyway, swim is following the way of Varma and Kabalka (Tetrahedron 46(21), 7443-7457 (1990)) to reduce nitrostyrenes to phenethylamines via NaBH4/BF3xEt2O refluxing for 5.5 hours.
After reexamination of the article at hand, swin noticed that N-Hydroxyphenethylamines are much easier to make via this method with only 1 hour reaction time and no reflux.
So swin will go ahead and will reduce some of his lovely styrene to 2,5-dimethoxy-N-hydroxyphenethylamine. and then swin will try to brominate and iodinate this material (iodination for all of u who are non-believers works nicely with KI/Oxone). So swin wants to know if this iodination or the regular bromination will cleave off the hydroxy group and leave swin with regular 2C-B/I, or make new hydroxyalted phenethylamines as desired???
Swin knows he can first brominate the benzaldehyde or iodinate and then reduce to the hydroxylated product, but as swin allready has the styrene, he would like to first try this. what do you all think?

Also, how would u think swin should brominate/iodinate the benzaldehyde? which tekniqks should work???

THANKS!!!