p-Fluoronitrobenzene → 4-(4-Nitrophenoxy)pyridine

HRID 2408390Notes

Reaction equation

HRID 2408390 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[N:5]1[CH:6]=[CH:7][C:2]([O:1][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178418642HCID 178418642, compound

Product 1

HCID 445585384-(4-Nitrophenoxy)pyridineYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxypyridine (4.42 g, 45.8 mmol) and 1-fluoro-4-nitrobenzene (4.89 mL, 45.8 mmol) in anhydrous DMF (50 mL) was added anhydrous K2CO3 (13.0 g, 91.6 mmol) in one portion. The mixture was heated at the reflux temperature with stirring for 24 h, cooled to room temperature and poured in water (300 mL). The solid that separated was filtered, washed with water and dried well under high vacuum to yield 8.9 g (90%) of desired product, 4-(4-pyridinyloxy)-1-nitrobenzene. 1H NMR (CDCl3, 300 MHz): δ 8.36 (d, 2H, J=9.0 Hz), 8.11 (d, 2H, J=8.1 Hz), 7.83 (d, 2H, J=9.0 Hz), 6.27 (d, 2H, J=7.8 Hz); LCMS (m/z): 217 (MH+).

Workup

  1. temperatureThe mixture was heated at the reflux temperature
  2. customThe solid that separated
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried well under high vacuum

Sources & evidence

ORD record
ord-881d8ddcf69d4ea1af85e77009aea5d0
Source dataset
uspto-grants-2014_08
Patent number
US08815848B2

Reaction notes

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