6161-61-1Relevant articles and documents
Products of reaction between tetrabromo-substituted ortho- and para-hydroxybenzoic acids and sodium nitrite in CH3COOH
Fadin,Tarasova,Vasin,Shishkin
, p. 1062 - 1070 (2013/01/15)
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.
POLYBROMINATED AROMATIC COMPOUNDS. IV. METHOXYDEBROMINATION REACTIONS OF POLYBROMOBENZENES IN PYRIDINE
Shishkin, V. N.,Lapin, K. K.,Tanaseichuk, B. S.,Butin, K. P.
, p. 516 - 522 (2007/10/02)
The rates were measured and the orientation was studied for the methoxydebromination of all polybromobenzenes C6HnBr6-n (n = 0-3) in pyridine at 115 deg C.From comparison of the partial rates of substitution of the bromine atom at various positions of the benzene ring it was found that the activating effect of the bromine atom in relation to the point of nucleophilic attack changes in the order o-Br > m-Br > p-Br, and the directing selectivity of the bromine is low (compared with fluorine in the methoxydefluorination of polyfluorobenzenes) and increases with decrease in the number of bromine atoms in the aromatic ring of the substrate.