4-Fluorophenol → 6-(4-Cyanophenoxy)-2-(4-fluorophenoxy)nicotinic acid ethyl ester

HRID 1024698Notes

Reaction equation

HRID 1024698 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[N:7][C:6]=1Cl)[CH3:2].[F:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1>>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[N:7][C:6]=1[O:29][C:26]1[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=1)[CH3:2]

Participants

3

Reactant 2

HCID 97324-FluorophenolHCID 86665953HCID 86665953, compound

Product 1

HCID 676077006-(4-Cyanophenoxy)-2-(4-fluorophenoxy)nicotinic acid ethyl esterYield 75%

Procedure

2-Chloro-6-(4-cyano phenoxy)nicotinic acid ethyl ester (0.25 g, 0.81 mmol) and 4-fluorophenol (0.09 g, 0.81 mmol) were coupled using the procedure of Example 17(b) to afford 0.23 g of the required product. Percentage purity (LCMS): 61.86%.

Sources & evidence

ORD record
ord-9b9e8f1a97ad40f69ed234e167c2d297
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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