4-Cyanophenol → 2-Chloro-6-(4-cyanophenoxy)-5-fluoro nicotinic acid ethyl ester

HRID 1024703Notes

Reaction equation

HRID 1024703 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([F:11])[C:8](Cl)=[N:7][C:6]=1[Cl:13])[CH3:2].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)#[N:16]>>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([O:23][C:20]2[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[CH:18][CH:19]=2)=[N:7][C:6]=1[Cl:13])[CH3:2]

Participants

3

Reactant 2

HCID 130194-CyanophenolHCID 13210747Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate

Product 1

HCID 866659552-Chloro-6-(4-cyanophenoxy)-5-fluoro nicotinic acid ethyl esterYield 49.9%

Procedure

2,6-Dichloro-5-fluoro-nicotinic acid ethyl ester (3.5 g, 15.0 mmol) and 4-cyano-phenol (1.78 g, 15.0 mmol) were coupled using the procedure of Example 17(a) to afford 2.4 g of the required product. 1H NMR (DMSO-d6): δ 1.35 (3H, t), 4.4 (2H, q), 7.58 (2H, d), 8.0 (2H, d), 8.4 (1H, d).

Sources & evidence

ORD record
ord-92be7361228b4607a8f3903434365453
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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