Print Page - feasible new route to p2ps?

Title: feasible new route to p2ps?
Post by: acid_egg on October 17, 2002, 10:43:00 PM

I found this brief reference hinting at another route to p2ps.Could it also be useful for ring substituted p2ps too?Is it feasible or useful and if so can someone with access post it plz?

"...Tri-n-butyl tin methoxide reacts with isopropenyl acetate to give,in situ acetonyl tri-n-butyltin which undergoes a Pd catalysed coupling reaction with aryl bromides[bromobenzene] to give aryl acetones[phenyl-2-propanone]...."

n-Bu₃SnOMe ArBr,PdCl2,P(o-tol)₃
AcOCH(CH2)CH3 --------------> n-Bu₃SnCH2COCH3 --------------> ArCH2COCH3

ref:Chem. Lett.,939 (1982)

Parts in red I have added.

Title: Expensive Envirotoxin
Post by: Rhodium on October 23, 2002, 12:14:00 AM

What's your price for the Bu₃SnOMe? I see Acros carry it for $30/25g (with "Toxic" and "Envirotoxin" ratings), and considering that the molar weight is 321 g/mole, it is costly to employ it in stoichiometric amounts.

The Pd complex is just used as a catalyst.

Title: ahhh...
Post by: acid_egg on October 23, 2002, 11:16:00 PM

it is costly to employ it in stoichiometric amounts

Ah..of course..thats the kicker!

I think it was listed in mine at ~$75/100g.
That envirotoxin bit sounds about right as I believe its used as 'defoulant' for boats.(for barnacles and such I suppose.)

Title: You can also use isopropenyl acetate to make p2p .
Post by: josef_k on November 07, 2002, 06:05:00 AM

You can also use isopropenyl acetate to make p2p from an aniline via the diazotonium. I'm not so sure if it works without an electron withdrawing group on the ring though. The patent I saw it in made 3-trifluoromethyl-p2p. If anyone is interested it is

Patent US5811586 (http://l2.espacenet.com/dips/viewer?PN=US5811586&CY=gb&LG=en&DB=EPD)

. Nevertheless it would be interesting to make the 4-tfm-amph.

The Vespiary

The Hive => Novel Discourse => Topic started by: acid_egg on October 17, 2002, 10:43:00 PM