Nitric Acid → HCID 67273342, compound

Participants

Reaction Steps

In SCHEME 7 4-bromoguaiacol (28) is selectively nitrated with 70% HNO3 in AcOH to give 4-bromo-6-nitroguaiacol (29) which is further methylated with methyl iodide and K2CO3 in acetone to give the corresponding 5-bromo-3-nitroveratrol (30). 5-bromo-3-nitroveratrol (30) is reacted under inert conditions with a boronic acid of generell type (31) under Suzuki-type basic conditions (Pd(PPh3)4 and aqueous sodium bicarbonate in dimethoxyethane) to a biaryl of type (32). Biaryl (32) is further hydrolized with aqueous lithium hydroxide in THF and MeOH or MeCN to give the corresponding carboxylic acid (33) which is converted to a building block of type (34) by reaction with oxalyl chloride in anhydrous dichloromethane.

Provenance & Evidence