Cesium carbonate → HCID 15661719, compound

HRID 1756325Notes

Reaction equation

HRID 1756325 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:9][O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 122742,6-DibromopyridineHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 15661719HCID 15661719, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2.37 g of 2,6-dibromopyridine and 1.52 g of 3-hydroxybenzoic acid methyl ester in 10 ml of dimethylformamide is mixed with 6.6 g of cesium carbonate and heated to 120° C. with stirring for 3 hours. The reaction mixture is filtered on diatomaceous earth, rewashed with dichloromethane and the filtrate is concentrated by evaporation in a vacuum. The residue is distilled on a bulb tube at 140°-150° C. and 0.04 mbar. 2.98 g of 3-(6-bromo-2-pyridyloxy)-benzoic acid methyl ester of melting point 68°-69° C. is obtained.

Workup

  1. filtrationThe reaction mixture is filtered on diatomaceous earth
  2. concentrationthe filtrate is concentrated by evaporation in a vacuum
  3. distillationThe residue is distilled on a bulb tube at 140°-150° C.

Sources & evidence

ORD record
ord-fb8bd01695044451ae2c6a37f0a081c3
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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