A PRACTICAL LARGE-SCALE PREPARATION OF 5'-BROMOSPIRO (CYCLOHEXANE-1, 3-[3H] INDOL)-2'(1'H)-ONE

…, A Rubezhov, JL Helorn, LR Routel…

Index: Wilk, Bogdan K.; Rubezhov, Arkadiy; Helom, Jean L.; Routel, Lisa R.; Potoski, John R. Organic Preparations and Procedures International, 2005 , vol. 37, # 3 p. 283 - 285

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Citation Number: 3

Abstract

The regioselectivity and purity problems were overcome by simply changing the order of transformations, ie introduction of bromine in the oxindole core followed by alkylation of 5- bromooxindole (2), 396 which was prepared from inexpensive, technical grade 5- bromoisatin (l).'It was found that n-butyllithium could be replaced with potassium tert- butoxide and 1, 5-diiodopentane with the more stable 1J-dibromopentane at 0 C in ...