Organic Lab Reactions 238

Organic Lab Reactions 238 - anilines or by coupling with...

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DERIVATIVES OF BIPHENYL 233 toluene and N-nitrosoacetanilide, 4-nitro-3-methylbiphenyl (IV) is ob- tained in 15 % yield. It is of interest that in the latter reaction coupling takes place para to the nitro group rather than para to the methyl group. The structure of the compound follows from its formation from the nitrosoacetyl derivative of 3-methyl-4-nitroaniline and benzene. N(NO)COCH 3 N(NO)COCH 8 The stabilized diazonium salt procedure has given 3,4'-dinitrobiphenyl (V) in 54% yield from m-nitroaniline and-nitrobenzene and 4,4'-dinitro- biphenyl (VI) in 69% yield from p-nitroaniline and nitrobenzene. NOJS NO 2 NO 2 VI Alkoxy derivatives of biphenyl can be obtained either from alkoxy-
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Unformatted text preview: 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 w prepared the highly substituted biphenyl compound, 2-cyano-5-methyl-2',5'-dimethoxy-4'-n-amylbiphenyl (VII), in 2 7 % yield from the nitrosoacetyl derivative of 2-cyano-5-methylaniline and 2,5-dimethoxy-ra-amylben-zene. CH 8 CH 3 CE^O \ \ •N(NO)COCH 3 + CN 0CH 3 » Ghosh, PascaU, and Todd, J. Chtm. Soc, 1940, 1118,...
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