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Home Molecular Biology Method-for-preparing-substituted-meta-phenylalkoxynitrobenzenes

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 Method for preparing substituted meta-phenylalkoxynitrobenzenes

Details
Inventors: Spatz, David M.;
Assignee: American Cyanamid Company (Stamford, CT)
Primary Examiner: Helfin; Bernard
Assistant Examiner:
Attorney, Agent or Firm: Monahan; Thomas J., Jackson; H. G.

Methods for the preparation of substituted meta-phenylalkoxynitrobenzenes and their use as starting materials for the synthesis of herbicidal meta-phenylalkoxyphenylurea.

DETAILED DESCRIPTION We claim: 1.
A method for the preparation of compounds of formula: ##STR15## wherein Y is hydrogen, halogen, C.
sub.
1 -C.
sub.
4 alkyl, C.
sub.
3 -C.
sub.
5 alkenyl, C.
sub.
3 -C.
sub.
5 alkynyl, C.
sub.
1 -C.
sub.
4 alkoxy, CH.
sub.
3 S, CF.
sub.
3, CN, NH.
sub.
2, OCF.
sub.
2 H, OCF.
sub.
3 or OCF.
sub.
2 Cl; Z is hyrogen, C.
sub.
1 -C.
sub.
4 alkyl, C.
sub.
1 -C.
sub.
4 alkoxy, halogen, or CF.
sub.
3 ; U is hydrogen, C.
sub.
1 -C.
sub.
4 alkyl, C.
sub.
1 -C.
sub.
4 alkoxy or halogen; A is C.
sub.
2 -C.
sub.
4 alkylene, straight chain or branched; comprising reacting a compound of formula: ##STR16## wherein Y, Z, U and A are as defined above with an equimolar amount of m-dinitrobenzene in the presence of an equimolar amount of an alkali metal hydroxide or an alkali metal alkoxide and in the presence of a polar solvent of hexamethylphosphoramide, dimethylformamide, dimethyl sulfoxide, acetonitrile or mixtures thereof in the temperature range of from 20.
degree.
C.
to 80.
degree.
C.
2.
A method according to claim 1, wherein Y is hydrogen, Cl, F, CH.
sub.
3 or CH.
sub.
3 O; Z and U are both hydrogen; the alkali metal alkoxide is potassium t-butoxide; the solvent is hexamethylphosphoramide, and the temperature range is 20.
degree.
C.
to 30.
degree.
C.
3.
The method according to claim 1, wherein the compound is 3-(phenylethloxy)nitrobenzene.
4.
A method according to claim 1, wherein the compound is 3-(4-methylphenylethyloxy)nitrobenzene.
5.
A method according to claim 1, wherein the compound is 3-(4-methoxyphenylethyloxy)nitrobenzene.
6.
A method according to claim 1, wherein the compound is 3-(4,.
alpha.
-dimethylphenylethyloxy)nitrobenzene.
7.
A method according to claim 1, wherein the compound is 3-(4,.
beta.
-dimethylphenylethyloxy)nitrobenzene.
8.
A method according to claim 1, wherein the compound is 3-(4-methoxy-.
alpha.
-methylphenylethyloxy)nitrobenzene.
9.
A method according to claim 1, wherein the compound is 3-(4-methoxy-p-methylphenylethyloxy)nitrobenzene.




Description:
The invention relates to methods for the preparation of compounds of formula (I): ##STR1## wherein Y is hydrogen, halogen, C



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