Post 528777 (https://www.thevespiary.org/talk/index.php?topic=9064.msg52877700#msg52877700)
(phenethyl_man: "sick of methylations? easy prepn. of anisoles.", Methods Discourse)Post 529886 (https://www.thevespiary.org/talk/index.php?topic=9947.msg52988600#msg52988600)
(Rhodium: "Cu(I) catalysed aromatic nucleophilic substitution", Methods Discourse)One-Step Preparation of Some 3-Substituted Anisoles
J. Zilberman, Org. Process Res. Dev. 7, 303-305 (2003)(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Abstract
A one-step preparation of 3-bromoanisole, 3-chloroanisole, and 3-trifluoromethylanisole from the corresponding 3-substituted nitrobenzenes is carried out by nucleophilic aromatic substitution of the nitro group with sodium or potassium methoxide, employing an effective amount of a phase-transfer catalyst (PTC), in a medium of a nonpolar aprotic solvent, under aerobic conditions, at a temperature of 50-65°C. The alkali methoxide used can be a pre-prepared solid, or it can be prepared in situ from the alkali hydroxide and methanol. The methoxydenitration proved to be very sensitive to the type of PTC. The effect of the solvent on the reaction is discussed. The targeted anisoles are obtained in yields of more than 80% and purities of greater than 99%.
Post 511796 (https://www.thevespiary.org/talk/index.php?topic=10688.msg51179600#msg51179600)
(pink_dust_angel: "sodium salt of alcohols", Newbee Forum)Post 512239 (missing)
(psyloxy: "some great alkali alkoxide patents", Chemistry Discourse)