Phenol → 5-Nitro-2-phenoxypyridine

HRID 1814640Notes

Reaction equation

HRID 1814640 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:8]([C:11]1[CH:12]=[CH:13][C:14](Cl)=[N:15][CH:16]=1)([O-:10])=[O:9].C(OCC)C>[OH-].[Na+].C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:15][CH:16]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 996PhenolHCID 3283Diethyl EtherHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 32523715-Nitro-2-phenoxypyridineYield 48.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

Phenol (0.9 g, 9.5 mmol) was dissolved in sodium hydroxide (50% solution, 12 mL). 5-Nitro-2-chloropyridine (1.5 g, 9.5 mmol) in toluene (15 mL) was added followed by addition of tetrabutylammonium bromide (0.3 g, 0.95 mmol). The reaction mixture was stirred for 16 hours at 20° C. and 5 hours at 80° C. where after it was cooled to room temperature and diethyl ether (100 mL) added. The organic phase was washed with water (5×50 mL), dried (MgSO4), and concentrated in vacuo to give 1.0 g of 5-nitro-2-phenoxypyridine.

Workup

  1. temperaturewas cooled to room temperature
  2. washThe organic phase was washed with water (5×50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f5e1ce1c5cb476aaae4318de4556d22
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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