Hydrogen Peroxide → 2-Bromo-4-chloro-5-fluoro-phenol

HRID 374610Notes

Reaction equation

HRID 374610 reaction equation
[Br:1][C:2]1[CH:18]=[C:17]([Cl:19])[C:16]([F:20])=[CH:15][C:3]=1C(C1C=CC=C([N+]([O-])=O)C=1)=O.OO.BrC1C=C(Cl)C(F)=CC=1C(O)=[O:27].[N+](C1C=C(O)C=CC=1)([O-])=O.[N+](C1C=C(C=CC=1)C(O)=O)([O-])=O>OS(O)(=O)=O.O=S(=O)=O.O>[Br:1][C:2]1[CH:18]=[C:17]([Cl:19])[C:16]([F:20])=[CH:15][C:3]=1[OH:27]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 84973-Nitrobenzoic acidHCID 111373-NitrophenolHCID 18997595HCID 18997595, compoundHCID 18997597HCID 18997597, compound

Product 1

HCID 189975962-Bromo-4-chloro-5-fluoro-phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24681Fuming sulfuric acidSolvent

Procedure

The reaction of 35.8 g (0.1 mol) of 2-bromo-4-chloro-5-fluoro-3'-nitrobenzophenone in 150 g of 5% oleum with 9.7 g (0.2 mol) of 70% hydrogen peroxide solution gives a mixture (29.0 g) of 2-bromo-4-chloro-5-fluorophenol, 2-bromo-4-chloro-5-fluorobenzoic acid, 3-nitrophenol and 3-nitrobenzoic acid (proportions in GC area-%: 14, 35, 36, 15) after dilution (300 g of water), refluxing for 4 h and extraction with methyl tert-butyl ether after removal of the solvent.

Sources & evidence

ORD record
ord-8c69ef1134da4ccda0367bea60bc6026
Source dataset
uspto-grants-1996_01
Patent number
US05481032

Reaction notes

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