Potassium Carbonate → 2-(3-Phenoxyphenoxy)-3-cyanopyridine

HRID 467042Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[O:7]([C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:22]1[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][N:23]=1>CN(C=O)C.[Cu]>[O:7]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[O:20][C:22]1[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][N:23]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of potassium carbonate (5.53 g, 0.04 mol) and 3-phenoxyphenol (15 g, 0.08 mol) in DMF (60 ml) was heated at 80° C. with stirring for 30 minutes. 2-Chloro-3-cyanopyridine (11.08 g, 0.08 mol) and copper bronze (0.8 g) were added and the resulting mixture heated at reflux for 90 minutes. GC analysis indicated the formation of a single product (96%). The reaction mixture was cooled and filtered, and then poured into water (300 ml) and allowed to stand over the weekend. The yellow-brown oily precipitate was extracted into dichloromethane and dried. The dichloromethane solution was then filtered and evaporated to yield crude 2-(3-phenoxyphenoxy)-3-cyano-pyridine (36.2 g, contaminated with DMF) which was used in the next stage without further purification.

Workup

temperaturethe resulting mixture heated
temperatureat reflux for 90 minutes
temperatureThe reaction mixture was cooled
filtrationfiltered
additionpoured into water (300 ml)
extractionThe yellow-brown oily precipitate was extracted into dichloromethane
customdried
filtrationThe dichloromethane solution was then filtered
customevaporated

Sources & evidence

ORD record: ord-b50908ce498541fd8ad711932b7cfabf
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05158954

Reaction notes

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