On August 22, 1995, James, Donald R.; Baker, Don R.; Mielich, Steven D.; Michaely, William J.; Fitzjohn, Steven; Knudsen, Christopher G.; Mathews, Christopher; Gerdes, John M. published a patent.Application In Synthesis of 4-Bromo-5-methoxy-2-methylaniline The title of the patent was Aryl indazoles, a process for producing them, and their use as herbicides. And the patent contained the following:
This invention relates to substituted arylindazoles I (R1 = H or halo; R2 = e.g., N, nitro, halo; R3 = e.g., H, halo; R4, R5, R6 are independently, e.g., H, halo, nitro, hydroxy, cyano; R7 = H, halo, C1-6 alkyl, nitro; R8 = H, halo), a process for producing them and their use as herbicides. Thus, e.g., 5-methoxy-2-methyl-4-nitroaniline was converted to 6-methoxy-5-nitroindazole by standard diazotization-cyclization route; arylation of the latter with 3,5-dichloro-4-fluorobenzotrifluoride afforded the 1-arylindazole I (R1-R8, X given resp. as: H, Cl, CF3, H, NO2, OMe, H, H, C-Cl) which exhibited 100% control pre-emergence of green foxtail, watergrass, wild mustard, and velvetleaf, and 100% control post-emergence of green foxtail, wild mustard, and velvetleaf. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Application In Synthesis of 4-Bromo-5-methoxy-2-methylaniline
The Article related to arylindazole herbicide, indazole aryl herbicide, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Application In Synthesis of 4-Bromo-5-methoxy-2-methylaniline
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem