Sodium hydride → Ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoate

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].[H-].[Na+].[Cl:16][C:17]1[CH:22]=[C:21]([N+]([O-])=O)[CH:20]=[CH:19][N:18]=1>>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:16])[CH:22]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 7351522-Chloro-4-nitropyridine

HCID 58847555Ethyl 4-chloro-3-hydroxybenzoate

Product 1

HCID 86634737Ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoateYield 53%

Procedure

Following the method of Example 3, Step A, ethyl 4-chloro-3-hydroxybenzoate (5.75 g, 28.7 mmol), sodium hydride (0.724 g, 28.7 mmol), DM (30 mL), and 2-chloro-4-nitropyridine (4.54 g, 28.7 mmol) were combined to give the desired product (4.75 g, 47.8% yield) as a yellow oil.

Sources & evidence

ORD record: ord-62f3a5404044455bbd14b7f7284840d0
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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