Nitrous acid-catalyzed nitration of 4-bromo-2, 5-dichlorophenol. Observation of an unusually facile rearrangement of a 4-bromo-2-nitrophenol during nitration

…, FW Hartner, RA Reamer, RP Volante

Index: Conlon, David A.; Lynch, Joseph E.; Hartner Jr., Frederick W.; Reamer, Robert A.; Volante Journal of Organic Chemistry, 1996 , vol. 61, # 18 p. 6425 - 6429

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Citation Number: 19

Abstract

During the development of a synthesis of the nonnucleoside, HIV-1 specific reverse transcriptase inhibitor, L-697,661 (1) 1, 2 we required easy access to the known 2- aminophenol (2). 2 There were several possible routes3 to the aminophenol 2, but we chose to examine the nitration of the readily available 4-bromo-2, 5-dichlorophenol (4), 4 to generate the 2-nitrophenol 3, expecting the 4-bromo substituent to undergo ...