Organic Lab Reactions 237

Organic Lab Reactions 237 - reaction between diazotized...

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232 THE PREPARATION OF UNSYMMETR1CAL BIARYLS NOj II structure is illustrated by the following five isomeric bromomethylbi- phenyls, which have been prepared from the corresponding bromo- toluidines and benzene. For the preparation of biphenyl compounds with substituents in only one ring, it is usually advisable to employ a substituted aniline and couple with benzene rather than to use aniline and couple with a benzene derivative, since with benzene only a single biaryl compound is produced. Thus, 4-methylbiphenyl can be isolated readily in pure form from the
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Unformatted text preview: reaction between diazotized p-toluidine and benzene, but not from the mixture of 2- and 4-methylbiphenyl formed from diazotized aniline and toluene. N 2 +C1- + Ni+Cl" + However, isolation of the product or products formed by coupling with nitrobenzene and certain other compounds has been successful. From nitrobenzene and diazotized aniline (in the form of the stabilized diazo-nium salt), 4-nitrobiphenyl is obtained in 33% yield, and from o-ni^ro-...
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