PREPARATION OF C14-LABELLED ACIDS FROM C14O2 AND ARYL LITHIUM COMPOUNDS

作者：A. C. Neish · 发表于：Canadian Journal of Biochemistry and Physiology · 年份：1959 · DOI：10.1139/o59-162 · 被引用次数：7 · 研究领域：Coordination Chemistry and Organometallics、Synthetic Organic Chemistry Methods、Asymmetric Hydrogenation and Catalysis

A simplified technique was developed for carbonation of Grignard reagents or organolithium compounds, with C14O2 generated from barium carbonate. 3,4-(Dibenzyloxy)-bromobenzene was treated with n-butyl lithium in ether and then with C14O2 to give 3,4-(dibenzyloxy)-benzoic acid-carboxyl-C14. The yield was 74% based on barium carbonate. 2,6-Dichlorobenzoic acid-carboxyl-C14 (yield 77%) and 3,5-dichlorobenzoic acid-carboxyl-C14 (yield 76%) were prepared from the corresponding dichlorobromobenzenes by a similar sequence of reactions. Attempts to synthesize 2,4- and 2,5-dichlorobenzoic acids by this route gave poor yields of unidentified acids, from which the expected products could not be isolated.