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ChemicalBook CAS DataBase List 4,5,9,10-Tetrabromoisochromeno[6,5,4-def]isochromene-1,3,6,8- tetraone

4,5,9,10-Tetrabromoisochromeno[6,5,4-def]isochromene-1,3,6,8- tetraone synthesis

2synthesis methods
-

Yield: 100%

Reaction Conditions:

with fuming sulphuric acid;sulfuric acid;bromine at 140; for 672 h;

Steps:


The synthesis of NDI-AQ (1) was achieved by reacting 1,4,5,8-naphthalenetetracarboxylic dianhydride (NDA) with 5.3 equiv ofBr2 in a mixture of sulfuric acid and oleum (v:v, 4:1) at 140 C for4 weeks. 2,3,6,7-Tetrabromonaphthalene diimide (3) was preparedover two steps by the reaction of 2 and 4 equiv of n-octylamine inrefluxing acetic acid for 30 min to give 2,3,6,7-tetrabromo-4,8-bis(octylcarbamoyl) naphthalene-1,5-dicarboxylic acid, whichwas further treated with excess PBr3 in refluxing toluene for 12 hto afford 3 in 31% overall yield.1

References:

Bobe, Sharad R.;Bhosale, Sidhanath V.;Jones, Lathe;Puyad, Avinash L.;Raynor, Aaron M.;Bhosale, Sheshanath V. [Tetrahedron Letters,2015,vol. 56,# 33,p. 4762 - 4766] Location in patent:supporting information