Products of reaction between tetrabromo-substituted ortho- and para-hydroxybenzoic acids and sodium nitrite in CH3COOH

Article abstract of DOI:10.1134/S1070428012080064

The reaction of 2,3,5,6-tetrabromo-4-hydroxybenzoic acid with a 10-fold excess of NaNO2 in the glacial acetic acid at 20°C affords tetrabromonitrosophenols whose further transformations under the reaction conditions leads to the formation of a mixture of 2,4,5,6-tetrabromo-p-quinone diazide and tetrabromo-p- and -o-nitrophenols in the molar ratio 37 : 2 : 1. Under similar conditions the 3,4,5,6-tetrabromo-2-hydroxybenzoic acid is converted into a mixture of 3,4,5,6-tetrabromo-o-quinone diazide with the same nitrophenols in the ratio 13 : 1 : 3. The reaction of sodium 2,3,5,6-tetrabromo-4-hydroxy-benzoate with NaNO2 in dilute acetic acid resulted in a quantitative yield of tetrabromo-p-quinone monooxime. Pleiades Publishing, Ltd., 2012.