Hydrochloric Acid → HCID 67297135, compound

HRID 215826Notes

Reaction equation

HRID 215826 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[OH:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].Cl>N1C=CC=CC=1.[Cu]I>[CH3:18][O:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([O:10][C:2]2[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 27348955-Bromo-2-methoxypyridine

Product 1

HCID 67297135HCID 67297135, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolvent

Procedure

A suspension of 5-bromo-2-methoxy-pyridine (5.9 g, 30 mmol), methyl 4-hydroxy-benzoate (4.0 g, 26 mmol), K2CO3 (4.7 g, 34 mmol), Cu powder (0.25 g, 4 mmol) and CuI (0.25 g, 1.3 mmol) in pyridine (25 ml) was refluxed for 10 h and allowed to cool to room temperature. The resulting mixture was poured in 100 g of crushed ice, neutralized with HCl to pH 7.5 and extracted with diethyl ether. The extract was evaporated in vacuo, the residue was separated by column chromatography on silica (eluent hexanes-ethyl acetate 8:1) to give 2.8 g (35%) of 4-(6-methoxy-pyridin-3-yloxy)-benzoic acid methyl ester as colorless oil.

Workup

  1. temperaturewas refluxed for 10 h
  2. extractionextracted with diethyl ether
  3. customThe extract was evaporated in vacuo
  4. customthe residue was separated by column chromatography on silica (eluent hexanes-ethyl acetate 8:1)

Sources & evidence

ORD record
ord-3d998b44c8ac4845b5513f068e9d07f0
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

Loading…