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US 5,856,576 AGranted
Aryne intermediates and a process for the preparation thereof
AssigneeAmerican Cyanamid Company
InventorsPhilip M. Harrington, Kenneth A. M. Kremer
Life of this patent
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Abstract
There are provided aryne intermediates of formula I, useful in the manufacture of herbicidal compounds. ##STR1## Also provided is a method to prepare the formula I intermediates via the palladium catalyzed coupling of an o-halonitrobenzene or o-haloaniline with 3-butyne-1-ol.
Claims23
A compound of formula I ##STR16## wherein R is H, CN, F, formyl, C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl or C.sub.1 -C.sub.3 alkylsulfonyl groups,
- C.sub.1 -C.sub.4 alkoxy optionally substituted with one or more halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl or C.sub.1 -C.sub.3 alkylsulfonyl groups,
- C.sub.1 -C.sub.4 alkylthio optionally substituted with one or more halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl or C.sub.1 -C.sub.3 alkylsulfonyl groups,
- C.sub.1 -C.sub.4 alkylsulfinyl optionally substituted with one or more halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl or C.sub.1 -C.sub.3 alkylsulfonyl groups,
- C.sub.1 -C.sub.4 alkylsulfonyl optionally substituted with one or more halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl or C.sub.1 -C.sub.3 alkylsulfonyl groups,
- C.sub.1 -C.sub.4 alkylcarbonyl optionally substituted with one or more halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl or C.sub.1 -C.sub.3 alkylsulfonyl groups,
- C.sub.1 -C.sub.4 alkoxycarbonyl optionally substituted by one or more halogen or C.sub.1 -C.sub.3 alkoxy groups,
- di(C.sub.1 -C.sub.4 alkyl)amino optionally substituted by one or more halogen or C.sub.1 -C.sub.3 alkoxy groups,
- di(C.sub.1 -C.sub.4 alkyl)aminocarbonyl optionally substituted by one or more halogen or C.sub.1 -C.sub.3 alkoxy groups,
- di(C.sub.1 -C.sub.4 alkyl)aminosulfonyl optionally substituted by one or more halogen or C.sub.1 -C.sub.3 alkoxy groups, or
- a heterocyclic ring having 2 to 6 carbon atoms and 1 to 3 nitrogen, oxygen or sulfur atoms and being optionally substituted on the carbon atoms with one or more fluorine, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl groups;
- X is NO.sub.2 or NR.sub.1 R.sub.2 ;
- Z is OH, Br, Cl or OSO.sub.2 R.sub.3 ;
- R.sub.1 and R.sub.2 are each independently hydrogen, formyl, acetyl, haloacetyl, CO.sub.2 R.sub.4 or benzyl optionally substituted on the aromatic ring with one to three fluorine, nitro, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy groups;
- and
- R.sub.3 and R.sub.4 are each independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl or phenyl optionally substituted with one to three fluorine, nitro, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy groups;
- or
- when X is NR.sub.1 R.sub.2, the acid addition salts thereof.
14 more elements
Dependencies are inferred from the claim text.