4-Hydroxybenzoic Acid → 4,6-Dibromo-2-(2'-hydroxy-5'-methylphenyl)benzotriazol

HRID 1460738Notes

Reaction equation

HRID 1460738 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[C:5]([N+:10]([O-])=O)[C:3]=1[NH2:4].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[NH2:21]C1C=CC(C(O)=O)=CC=1[N+]([O-])=O.OC1C=CC(C(O)=O)=CC=1>>[Br:1][C:2]1[C:3]2[C:5](=[N:10][N:21]([C:16]3[CH:15]=[C:14]([CH3:13])[CH:19]=[CH:18][C:17]=3[OH:20])[N:4]=2)[CH:6]=[C:7]([Br:9])[CH:8]=1

Participants

5

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 2879P-CresolHCID 700092,4-Dibromo-6-nitroanilineHCID 74115Benzoic acid, 4-amino-3-nitro-

Product 1

HCID 199825084,6-Dibromo-2-(2'-hydroxy-5'-methylphenyl)benzotriazolYield 60%

Procedure

Example 1 was repeated except that 59.2 g (200 mmoles) of the 2,4-dibromo-6-nitroaniline and 21.6 g (200 mmoles) of p-methylphenol were used instead of 36.4 g (200 mmoles) of 4-amino-3-nitrobenzoic acid and 27.6 g (200 mmoles) of p-hydroxybenzoic acid respectively to obtain 4,6-dibromo-2-(2'-hydroxy-5'-methylphenyl)benzotriazol. The yield was 60%.

Sources & evidence

ORD record
ord-acf11270369d43918d5f936af41c2041
Source dataset
uspto-grants-1991_12
Patent number
US05071995

Reaction notes

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