Hodgson, H. H.; Wignall, J. S. published an article in 1927, the title of the article was Nitrosation of phenols. IV. 3,5-Dichlorophenol.COA of Formula: C7H5Cl2NO3 And the article contains the following content:
cf. C. A. 20, 3449. Nitration of 16 g. 3,5-Cl2C6H3OH with NaNO3 and dilute H2SO4 gives 5 g. 3,5-dichloro-2-nitrophenol (I), lemon-yellow, m. 51°, volatile with steam, does not give a solid Ac derivative, and 6 g. 3,5,4-Cl2(O2N)C6H2OH (II), m. 150°, whose acetate, m. 99°. The action of HNO2 on 3,5-Cl2C6H3OH gives II. Reduction of I gives the 2-amino derivative, m. 132°; the 4-amino derivative; m. 154°; the 2 isomers give reddish brown and violet colors with FeCl3. I or II, with Me2SO4, gives 70% of the corresponding anisoles, m. 75° and 70°, resp. 3,5-Dicloro-4-aminoanisole, m. 71°. 3,5-Dichloro-4-nitrosoanisole, m. 125°, results by oxidation of the NH2 derivative with Caro’s acid; it turns green on melting but becomes colorless on cooling; heating with concentrated H2SO on the H2O bath for 0.5 hr. gives 3,5-dichloro-4-nitrosophenol [quinone-4-oxime (?) ], decomposes 165°; boiling acids decompose it. Reduction of 3,4-Cl(O2N)C6H3OMe with Sn and HCl gives 3,5,4-Cl2(H2N)C5H2OMe. 3-Chloro-4-nitrosoanisole, deep green, m. 59°, results when the HCl salt of the 4-NH2 derivative is oxidized with K2S2O5 in AcONa solution 3,5-Dichloro-4-nitrodimethylaniline, golden, m. 142°, results from NaNO2 in HCO2H or from HNO3-H2SO4 at 0°. The experimental process involved the reaction of 1,5-Dichloro-3-methoxy-2-nitrobenzene(cas: 74672-01-8).COA of Formula: C7H5Cl2NO3
1,5-Dichloro-3-methoxy-2-nitrobenzene(cas:74672-01-8) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. COA of Formula: C7H5Cl2NO3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics