Natural Science Forum / Chemistry / Organic Synthesis / July 2005

Old references:

 Sam, G et al.,J.O.C.,1958, 23, 1500
 Grafe, I et al.,Chem. Ber.,1973, 106, 1724
 Takeda, K et al.,Synth. Commun.,1982, 12, 213
 Kim, S et al.,Heterocycles,1986, 24, 1625

Search patents too.

Pavel

Well, you can buy 4-chloro-2-aminophenol (CAS RN 95-85-2), perhaps
that'll cyclise in a similar fashion to making Evans' chiral
auxiliaries with diethyl carbonate or similar. Maybe even with
urea - see e.g. Gokhan, Aktay and Erdogan (accents suppressed here
unfortunately)
<URL:http://journals.tubitak.gov.tr/chem/issues/kim-04-28-1/kim-
28-1-14-0306-2.pdf> or <URL:http://snipurl.com/g68i>

Turk. J. Chem, 28, (2004), 123

Failing that (if the trisubstituted benzene is too pricey),
perhaps try nitration of p-chlorophenol and chemoselective
reduction of the nitro group will give the required in I assume
reasonable yield.

Any joy with the 2-chloropyridine N-oxide stuff?

Stephan

why not just buy it from Sigma?