4-Bromofluorenone was obtained from diphenic acid through fluorenone-4-carboxylic acid. It was further converted into 4, 9-dibromofluorene which was changed to 4, 4'-dibromo-bisdiphenyleneethylene by alkali. 4, 4', 4''-Tribromotribiphenylenepropane was synthesized by Michael condensation of the ethylene and 4-bromofluorene. Similarly, 4'-bromotribiphenylenepropane was obtained from bisdiphenyleneethylene and 4-bromofluorene. Thermal decomposition of these compounds yielded 4-bromofluorene, 4, 4'-dibromobisdiphenyleneethylene and-ethane, and bisdiphenyleneethylene and-ethane etc., these compounds being separated and confirmed respectively.
A. o-Anisidine diazotized is coupled with 2-naphthol, 3-hydroxy-2-naphthanilide, acetoacetanilide, or 1-phenyl-3-methyl-5-pyrazolone, to obtain azo-dyes. Each of the azo-dyes is chloromethylated in acetic acid solution by paraformaldehyde and dry hydrogen chloride gas in the presence of zinc chloride anhydride as a catalyst to obtain chloromethyl compounds. B. 2-Methoxy-5-hydroxymethylaniline synthesized by using o-nitroanisole as a starting material, is diazotized, it is coupled, with 2-naphthol, 3-hydroxy-2-naphthoanilide, acetoacetanilide, or 1-phenyl-3-methyl-5-pyrazolone, to obtain diazo-compounds. Each of the diazo-compounds is chlorinated in chlorobenzene solution by phosphorus pentachloride for conversion of the hydroxymethyl group into the chloromethyl group obtaining chloromethyl compounds. C. We confirmed that the chloromethyl compounds obtained by the method A and each of the corresponding compounds obtained by the method B are identical. We also succeeded to ccnfirm the positions of chloromethyl group obtained by the method A.