Holleman, A. F.; van Haeften, F. H. published an article in 1921, the title of the article was Replacement of substituents in the benzene ring. V. The six trichloronitrobenzenes and the three trinitrobenzenes; their reaction with sodium methylate.Computed Properties of 74672-01-8 And the article contains the following content:
Preparation of the 6 trinitrobenzenes. The 6 isomers are already described in the literature but the method of preparation was improved in several instances and the details are here given. Qualitative results on the action of NaOMe on the trichloronitrobenzenes. The methods used in this reaction were described previously (C. A. 15, 65). In this case the reaction is much slower than with the dichlorodinitrobenzenes so that heating some hrs. on the H2O bath is necessary. 15 g. 2,3,4-Cl3C6H2NO2 (A) after heating with 105 cc. 0 4755 N NaOMe solution 5 hrs. in an autoclave at 110° were poured into H2O and filtered. The product was distilled with steam and on crystallization from EtOH gave 3,4,2-Cl2(O2N)C6H6OMe, silky needles, m. 72.5°, identical with that obtained by d. Hollander (C. A. 15, 65). 5 g. 3,4,5-Cl3C6H2NO2 (B) heated 6 hrs. under a condenser on the H2O bath with 52 cc. NaOMe (0.47 N) gave after evaporating most of the MeOH and pouring into H2O a solid which from EtOH gave silky needles with a green reflex, m. 98°, identical with the Cl2(O2N)C6H2OMe obtained by d. H. (l. c.) from 1,3,2,5-C6H2Cl2(NO2)2. 20 g. 2,5,6-C3C6H2NO2 (C) were heated with 210 cc. NaOMe (0.47 N) 24 hrs. on a H2O bath under a condenser and after evaporating most of the MeOH the mixture was poured into H2O and filtered. The oil separated was distilled with steam and gave colorless crystals of 3,4,2-Cl2(O2N)COH2OMe, m. 128°. The main portion gave crystals of 2,5,6-Cl3C6H2OMe, m. 42.8°. 5 g. 2,4,5-Cl3C6H2NO2 (D) were heated with 52 g. NaOMe (0.47 N) for 6 hrs. on the H2O bath and gave a 2,5,4- Cl2(O2N)C6H2OMe, m. 101°, identical with that obtained from 1,4,2,5-C6H2Cl2(NO2)2. Beilstein and Kurbatow (Ann. 192, 23(1878)) found that with NH3 the Cl ortho to the NO2 group is replaced. 2,3,5-Cl3C6H2NO2 (E) with NaOMe gave the same anisole, m. 44°, obtained by d. H. from 1,3 5,6-C6H2Cl2(NO2)2. 6 g. 2,4,6-Cl3C6N2O2 (F) heated 6 hrs. with 65 cc. NaOMe on the H2O bath gave an anisole, m. 72.5°, which by arguments based on analogy is said to be 2,4,6-Cl2(MeO)C6H2NO2. Quantitative researches. The methods used were the same as those used by d. H. (l. c.) and the numerical results are given in table. Discussion of results. The numerical results are summarized in several tables. The reaction constants at 0 ° of chloronitrobenzenes, dichloronitrobenzenes, trichloronitrobenzenes and chlorodinitrobenzenes increase in the same order. The Cl atom which leaves the ring is always o- or P- with respect to the NO2 group. In each group of isomers the largest constant of reaction is obtained for that compound in which the Cl atom which leaves is in the P-position with respect to the NO2 group which it renders mobile. When another Cl atom is placed o- or p- to the Cl atom which leaves the mobility of the latter is increased. The conclusion of d. H. (l. c.) that in m-C6H4(NO2)2, m-ClC6H4NO2 and sym-Cl2C6H3NO2, which are inert toward NaOMe, any of the substituents is rendered mobile by the introduction of a NO2 group or a Cl atom, was fully confirmed. When one introduces a substituent it is always this which reacts with NaOMe. C and F showed the smallest velocity of reaction. The same is true of 2,6-Cl2C6H3NO2, showing that a NO2 group placed between 2 adjacent Cl atoms determines a very slow velocity of substitution. The fact that the velocity with C is less than with F shows that the presence of 3 Cl atoms adjacent diminishes the liberating activity of a NO2 group. The examination of the products of the transformation of C with NaOMe shows that in this isomer the NO2 group is changed in character. Comparison of the results for isomers of Cl2C6H3NO2 and Cl3C6H2NO2 shows that the latter behave more like Cl2C6H3NO2 derivatives than like Cl3C6H2NO2 derivatives The quant. conclusions are among the parts of the paper that cannot be adequately abstracted. Preparation of isomeric trinitrobenzenes. The details of the preparation of the 1,2,4-(G), 1,2,3- (H), and 1,3,5-trinitrobenzenes (I) are given here, although all were previously known. 5 g. H with 55 cc. 0.47 N NaOMe reacted at room temperature and after 0. 5 hr. on the H2O bath and after standing 24 hrs. separated 2,6-(O2N)2C6H8OMe, m. 118°. 5 g. G treated similarly gave 2,4-(O2N)2C6H8OMe, m. 88°. 5 g. I treated similarly gave 3,5-(O2N)2C63OMe, m. 105°. Data on quant. measurements of the same reactions are given. The experimental process involved the reaction of 1,5-Dichloro-3-methoxy-2-nitrobenzene(cas: 74672-01-8).Computed Properties of 74672-01-8
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. Computed Properties of 74672-01-8
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics