2- Bromo-4-methylaniline, diazotization

Alkoxy derivatives of biphenyl can be obtained either from alkoxy-anilines or by coupling with alkoxybenzenes. From diazotized p-bromo-aniline and anisole a 20% yield of 4-bromo-2 -methoxybiphenyl and a 7% yield of 4-bromo-4 -methoxybiphenyl are obtained. In connection with their studies on Cannabis Indica, Ghosh, Pascall, and Todd u prepared the highly substituted biphenyl compound, 2-cyano-5-methyl-2, 5 -dimethoxy-4 -n-amylbiphenyl (VII), in 27% yield from the nitrosoacetyl derivative of 2-cyano-5-methylaniline and 2,5-dimethoxy-n-amylben-zene. 

Another side reaction which occurs is reduction in the reaction the —N2C1 or —N(NO)COCH3 group is replaced by hydrogen. wi-Bromo-toluene was isolated in 6% yield from the reaction between the sodium diazotate from 2-bromo-4-methylaniline and benzene, and in 10% yield in a similar reaction from 2-methyl-4-bromoaniline.4 Some nitrobenzene is obtained in the preparation of 3-nitrobiphenyl from nitroso-w-nitro-acetanilide (p. 250). The source of the hydrogen effecting the reduction has not been determined. f... 

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