Phenol → 4-Bromo-2-phenoxybenzoic acid

HRID 2351119Notes

Reaction equation

HRID 2351119 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](=[O:11])([O-])[O-:9].[K+].[K+].[Br:14][C:15]1[CH:16]=[C:17](C(OC)=O)[C:18](CBr)=[CH:19][CH:20]=1>CN(C)C=O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:8]([OH:9])=[O:11])=[C:17]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Product 1

HCID 230539204-Bromo-2-phenoxybenzoic acidYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenol (8 g, 85 mmole) and potassium carbonate (11.7 g, 85 mmole) in 150 mL of N,N-dimethylformamide was reacted with methyl 4-bromo-α-bromo-2-toluate (20 g, 65 mmole) by the procedure of Example 2, step a and folloed with alkaline hydrolysis by the procedure of Example 2, step b to give the crude 4-bromo-2-phenoxybenzoic acid (13 g) which was used without further purification.

Workup

  1. customfolloed with alkaline hydrolysis by the procedure of Example 2, step b

Sources & evidence

ORD record
ord-ee8463b0b4404014abef61bf7e9bab42
Source dataset
uspto-grants-1989_10
Patent number
US04871865

Reaction notes

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