If after bromination the compound is insoluble in any of the common solvents like THF, DCM, DMF etc, then how to carry out Sonogashira coupling ?
Dear Ushasri Chilakamarthi,
Sonogashira coupling reaction carried out by use of solvents such as THF, DMF or bases like Et3N, diisopropyl amine. The alkyl amine serves both as base and solvent. The bromo derivative can be insoluble in common solvents; however, it can be partially soluble at elevated temperature (100-110 degree). That may be beneficial for the successful formation of product. If the reaction do not work, a mixture of solvent can be employed, for example, DMF and trialkyl amine (10:1) or toluene and trialkyl amine. The use of solvent DMF or toluene can be selected based on the polar nature of bromo substrates. If the derivative have any other polar functional group, DMF and base would serve better. If not, toluene can replace DMF.
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