76361-99-4Relevant articles and documents
REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. XIII. DIRECTION OF HYDROXYLATION OF 2-HALONITROBENZENES BY POTASSIUM HYDROXIDE
Malykhin, E. V.,Kolesnichenko, G. A.,Shteingarts, V. D.
, p. 1149 - 1152 (2007/10/02)
The reaction of 2-fluoronitrobenzene with potassium hydroxide and molecular oxygen in liquid ammonia at -33 deg C gave 2-nitrophenol.In contrast to 2-fluoronitrobenzene, both the halogen and hydrogen in the ortho and para positions to the nitro group are replaced in the reactions of 2-chloro- and 2-bromonitrobenzenes, KOH, and O2.In the case of 2-bromonitrobenzene, there is significant formation of a compound, formally corresponding to reductive dehalogenation (nitrobenzene and its hydroxylation product, 4-nitrophenol) and bromination of the nitrophenols formed in the position to the hydroxy group.