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

The reaction of 2,3,5,6-tetrabromo-4-hydroxybenzoic acid with a 10-fold excess of NaNO 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 NaNO in dilute acetic acid resulted in a quantitative yield of tetrabromo- p-quinone monooxime. [ABSTRACT FROM AUTHOR]