Sodium hydride → HCID 86634743, compound

HRID 911005Notes

Reaction equation

HRID 911005 reaction equation
[F: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>>[F: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

4

Reactant 3

HCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridineHCID 18007712Ethyl 4-fluoro-3-hydroxybenzoate

Product 1

HCID 86634743HCID 86634743, compoundYield 89%

Procedure

Using the method of Example 3, Step A, ethyl 4-fluoro-3-hydroxybenzoate (2.90 g, 15.8 mmol), 60% sodium hydride in mineral oil (631 mg, 15.8 mmol), and 2-chloro-4-nitropyridine (2.50 g, 15.8 mmol) were reacted to provide ethyl 4-fluoro-3-(2-chloropyridin-4-yloxy)benzoate (4.15 g, 89% yield) as a clear oil. 1H NMR-(CDCl3) δ 8.27 (d, 1H), 8.02 (m, 1H), 7.90 (d, 1H), 7.30 (t, 1H), 6.78-6.83 (m, 2H), 4.39 (q, 2H), 1.40 (t, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7e5db5cbb31244eba563701afe62e645
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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