Multikilogram-scale synthesis of a biphenyl carboxylic acid derivative using a Pd/C-mediated Suzuki coupling approach

DS Ennis, J McManus, W Wood-Kaczmar…

文献索引：Ennis, David S.; McManus, Julie; Wood-Kaczmar, Wladyslaw; Richardson, John; Smith, Gillian E.; Carstairs, Alexis Organic Process Research and Development, 1999 , vol. 3, # 4 p. 248 - 252

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被引用次数: 116

摘要

Reaction of 4-bromo-3-methylaniline with 4-chlorobutyryl chloride/TEA and subsequent treatment of the resulting secondary amide intermediate with KO t-Bu gives 1-(4-bromo-3- methylphenyl) pyrrolidin-2-one in 65% yield. This procedure has been optimised (74-76% overall yield) and has been carried out on 41 molar scale. In a variation of this process, we have employed NaOH as the ring-closing base under phase-transfer conditions. NaOH is ...