The author of 《Nitration of 3,5-dichlorobenzaldehyde and 3,5-dichlorobenzoic acid》 were Asinger, Fritz. And the article was published in Monatshefte fuer Chemie in 1933. Computed Properties of C7H3Cl2NO3 The author mentioned the following in the article:
3,5-Cl2C6H3CHO (10 g.) and 100 cc. HNO3 (d. 1.48) at room temperature for 3-4 hrs. give 99% (crude yield) of 2-nitro-3,5-dichlorobenzaldehyde (I), m. 91.5°; oxidation gives 3,5,2-Cl2(O2N)C6H2CO2H, m. 194° I yields an aldoxime, m. 97°, and a phenylhydrazone, blood-red, m. 175°. I and PCl5 in C6H6 give 2-nitro-3,5-dichlorobenzal chloride, m. 45°; this also results by nitration of 3,5-Cl2C6H3CHCl2. I, heated with Ac2O and AcONa 7 hrs. at 180°, gives 65% of 2-nitro-3,5-dichlorocinnamic acid, pale yellow, m. 227°. I and NAOH in Me2CO give 97% of 5,7,5′,7′-tetrachloroindigo. Reduction of I with FeSO4 and NH4OH gives 84% of the 2-NH2 derivative, pale yellow, m. 123°; aldoxime, m. 175°; phenylhydrazone, yellow-green, m. 118°. 3,5-Cl2C6H3CO2H and HNO3 (d. 1.48) at 70° give 83% of the 2-NO2 derivative (II), m. 194°; the Ca salt seps. with 4.5 mols. H2O; the Ba salt has 2.5 mols. H2O; the Ag salt is anhydrous; acid chloride, m. 94.5°; amide, m. 180°; Me ester, m. 73°; Et ester, m. 69°. Reduction of II gives the 2-NH2 derivative, m. 230-1° (98% yield). In the experiment, the researchers used 3,5-Dichloro-2-nitrobenzaldehyde(cas: 59178-12-0Computed Properties of C7H3Cl2NO3)
3,5-Dichloro-2-nitrobenzaldehyde(cas: 59178-12-0) belongs to organochlorine compounds. 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.Computed Properties of C7H3Cl2NO3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics