Phenol → HCID 20085921, compound

HRID 1608467Notes

Reaction equation

HRID 1608467 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:23](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]([CH2:23][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 20085921HCID 20085921, compoundYield 65.1%

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 6, step a and followed with alkaline hydrolysis by the procedure of Example 6, step b to give the crude 4-bromo-2-(phenoxymethyl)benzoic acid (13 g) which was used without further purification.

Workup

  1. customfollowed with alkaline hydrolysis by the procedure of Example 6, step b

Sources & evidence

ORD record
ord-a97b8e2eb1124893989be6a8a374e5b7
Source dataset
uspto-grants-1995_03
Patent number
US05395610

Reaction notes

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