M Bromotoluene

An example of this is given in Section IV.63—the conversion of 3-bromo-4-aminotoluene into m-bromotoluene. Another application is to the preparation of. iM.-tribromobenzene (Section IV,72) ... 

Three regioisomers (o m and p methylamline) were formed from m bromotoluene CH3 CH3 CH3 CH3... 

Problem 16.18 Treatment of p-bromololuene with NaOH at 300 °C yields a mixture of two products, but treatment of m-bromotoluene with NaOH yields a mixture of three products. Explain. 

A uV-Diethyl-m-toluamide (DEET) is the active ingredient in many insect-repellent preparations. Plow might you synthesize this substance from m-bromotoluene ... 

Problem 11.30 Account for the observation that NaOH reacts at 300 "C with p-bromotoluene to give m- and p-cresols, while m-bromotoluene yields the three isomeric cresols. A... 

The benzyne intermediate from p-bromotoluene has a triple bond between and C" both C s are independently attacked by OH, giving a mixture of m- and p-cresols (HOCtH CH,). Two isomeric benzynes are formed from m-bromotoluene, one with a C -to-C triple bond and the other with a C -to-C" triple bond. Hence, this mixture of benzynes reacts with OH at all three C s, giving the mixture of three isomeric cresols. 

For the preparation of m-bromotoluene, the following sequence of reactions from p-toluidine may be used ... 

The following couples were tested p-chlorobenzonitrile/p-chloro-acetophenone, p-chloroacetophenone/p-chlorodiphenyl, p-chlorodiphenyl /chlorobenzene, p-chlorodiphenyl/p-chlorofluorobenzene, chlorobenzene /p-chlorotoluene, chlorobenzene/p-chloroanisole, p-chloroacetophenone/ methyl ester of m-chlorobenzoic acid, chlorobenzene/m-chlorotoluene, p-chlorodiphenylether/p-chlorotoluene, m-chlorodiphenylether/chloroben-zene, m-chlorodiphenylether/p-chlorotoluene, chlorobenzene/methyl ester of m-chlorobenzoic acid, chlorobenzene/p-bromoanisole, p-bromoaceto-phenone / p-chlorobenzonitrile, p-bromobenzonitrile / p-chloroacetophe-none, bromobenzene/p-chlorodiphenyl, m-bromotoluene/chlorobenzene, and p-chlorodiphenyl/p-bromotoluene. 

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