Phenol → 5-Nitro-2-phenoxypyridine

HRID 1633913Notes

Reaction equation

HRID 1633913 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 tetra-butylammonium 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-40d00b8e59014abe9289a215a5075bf5
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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