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Synthesis of 5‐Substituted Resorcinol Derivatives via Cross‐Coupling Reactions
Author(s) -
Dol Georg C.,
Kamer Paul C. J.,
van Leeuwen Piet W. N. M.
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199802)1998:2<359::aid-ejoc359>3.0.co;2-n
Subject(s) - resorcinol , chemistry , stille reaction , reagent , boronic acid , organic chemistry , coupling reaction , suzuki reaction , catalysis , palladium
Suzuki and Stille cross‐coupling reactions were utilized in the synthesis of 5‐substituted 1,3‐dimethoxybenzene and 5‐substituted resorcinol derivatives. The substituted resorcinol derivatives were obtained in only three steps from inexpensive reagents. 1,3‐Dimethoxybenzoic acid and 1‐chloro‐3,5‐dimethoxybenzene were transformed into 1‐iodo‐, 1‐bromo‐, 1‐trimethyltin‐3,5‐dimethoxybenzene and 3,5‐dimethoxyphenyl boronic acid. 5‐Allyl‐1,3‐dimethoxybenzene and 3,5‐dimethoxybiphenyl derivatives were obtained via cross coupling reactions under mild conditions. HI, BBr 3 and AlI 3 were used to demethylate these dimethoxybenzenes into their resorcinol derivatives.