4,7-dibromo-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole → 2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole

HRID 1050680Notes

Reaction equation

HRID 1050680 reaction equation
BrC1C2C(=NN(C3C=CN=CC=3)N=2)C(Br)=CC=1.Br[C:19]1[C:27]2[C:23](=[N:24][N:25]([C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)[N:26]=2)[C:22](Br)=[CH:21][CH:20]=1>>[N+:34]([C:31]1[CH:32]=[CH:33][C:28]([N:25]2[N:26]=[C:27]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]3=[N:24]2)=[CH:29][CH:30]=1)([O-:36])=[O:35]

Participants

3

Reactant 2

HCID 866799014,7-dibromo-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazoleHCID 866799034,7-dibromo-2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole2×

Product 1

HCID 126917272-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazoleYield 16%

Procedure

A similar two-step procedure as that of Intermediate A was applied to give 2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole (16% yield) in the first step and 4,7-dibromo-2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole (Intermediate C, 75%) in the second step. 1H NMR (400 MHz, CDCl3): δ 8.65 (m, 2H, 4-nitrophenyl), 8.44 (m, 2H, 4-nitrophenyl), 7.54 (s, 2H, benzotriazole).

Sources & evidence

ORD record
ord-48cad46c02b541f99805573790c2a5b5
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Reaction notes

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