Dimethylformamide → 5-Bromo-2,4-dimethoxybenzoic acid

HRID 2410247Notes

Reaction equation

[Br:1][C:2]1[C:3](O)=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].IC.[C:15](=O)([O-])[O-].[Cs+].[Cs+].CN(C)[CH:23]=[O:24]>>[Br:1][C:2]1[C:3]([O:24][CH3:23])=[CH:4][C:5]([O:11][CH3:15])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 10796Cesium carbonate

HCID 818145-Bromo-2,4-dihydroxybenzoic acid

Product 1

HCID 135050975-Bromo-2,4-dimethoxybenzoic acid

Procedure

1.1 A solution of 15 g of 5-bromo-2,4-dihydroxybenzoic acid, 14.4 ml of iodomethane and 62.9 g of caesium carbonate in 100 ml of N,N-dimethylformamide (DMF) is heated under reflux for 16 hours. The mixture is subjected to conventional work-up, giving 16.7 g of 5-bromo-2,4-dimethoxybenzoic acid (“1”).

Workup

temperatureunder reflux for 16 hours

Sources & evidence

ORD record: ord-e72a2cfced644ffcabb47167e511f227
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816070B2

Reaction notes

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