Phenol → 2-Chloro-4-phenoxypyridine

HRID 910901Notes

Reaction equation

HRID 910901 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:10][C:11]1[CH:16]=[C:15]([N+]([O-])=O)[CH:14]=[CH:13][N:12]=1>>[Cl:10][C:11]1[CH:16]=[C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 117889672-Chloro-4-phenoxypyridineYield 98%

Procedure

Using the method of Example 3, Step A, phenol (494 mg, 6.31 mmol), 60% sodium hydride in mineral oil (252 mg, 6.31 mmol), and 2-chloro-4-nitropyridine (1.00 g, 6.31 mmol) were reacted to provide 2-chloro-4-phenoxypyridine (1.27 g, 98% yield) as an oil. 1H NMR (CDCl3) δ 8.22 (d, 1H), 7.45 (t, 2H), 7.29 (t, 1H), 7.09 (d, 2H), 6.77-6.82 (m, 2H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6663ccd7310944d4b28926df45502a17
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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