CCXCIX.—Chlorination of benzoyl chloride. Part I

Abstract

By EDWARD ITOPE a i d GEORGE CLIFFORD RILEY. AMONG the problems concerning the influence of the character of an atom or group, substituted in the benzene ring, on the position taken up by another atom or groiip entering the ring,

Synthesis of Halogenated Anilines by Treatment of N,N-Dialkylaniline N-Oxides with Thionyl Halides

“…Aryl halides are also common substructures in synthetic and naturally occurring biologically active molecules and constitute some end-user industrial materials as well . Classical methods of preparing aryl halides (e.g., electrophilic aromatic substitution) are prone to complications in electron-rich settings; , aniline and phenol substrates are highly reactive toward electrophilic halogenation reagents, often compromising the regioselectivity or stoichiometry of the resultant reactions . Thus, new synthetic methods for the regioselective halogenation of electron-rich aromatics are of high utility in synthetic organic chemistry.…”

The Reactivity of Atoms and Groups in Organic Compounds. V. Third Contribution on the Carbon-Chlorine Bond: The Rates of the Reactions of Certain Derivatives of Diphenylchloromethane With Ethyl Alcohol

“…The melting point agrees with that obtained with the product formed by reducing m-methylbenzophenone with sodium amalgam16, and not with that of a substance described as this compound by E. and O. Fischer.17 ra-Methyldiphenylchloromethane prepared from the carbinol is a colorless oil; Cl found, 16.20 and 16.22; caled., 16.37%. m-Chlorodiphenylchloromethane.-m-Chlorobenzoyl chloride was prepared by the method of Hope and Riley. 18 The crude product was distilled at 10 mm. pressure and the fraction boiling below 100°was fractionated four times at atmospheric pressure.…”