3-Cyanophenol → HCID 10733955, compound

HRID 612508Notes

Reaction equation

HRID 612508 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)#[N:4].F[C:13]1[CH:18]=[CH:17][CH:16]=[C:15](F)[N:14]=1>CN(C)C=O>[N:14]1[C:15]([O:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]#[N:4])=[CH:16][CH:17]=[CH:18][C:13]=1[O:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]#[N:4]

Participants

5

Reactant 3

HCID 133943-CyanophenolHCID 24758Sodium hydrideHCID 739342,6-Difluoropyridine

Product 1

HCID 10733955HCID 10733955, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To sodium hydride (0.38 g, 9.5 mmol) in N,N-dimethylformamide (3 mL) was added 3-cyanophenol (1.1 g, 8.9 mmol) and 2,6-difluoropyridine (0.4 mL, 4.4 mmol). After heating in an oil bath at 100° C. for 15 hours the reaction was partitioned with ethyl acetate and water. The organic layer was separated, washed with water, dried (Na2SO4), and the solvent was removed in vacuo. The residue was chromatographed on silica gel (50 g) with methylene chloride/hexane (3/1) to give 3,3'-[2,6-pyridinediylbis(oxy)]bis(benzonitrile). Recrystallization from ethyl acetate/hexane gave pure 3,3'-[2,6-pyridinediylbis(oxy)]bis(benzonitrile); NMR (CDCl3) 7.79 (t,1), 7.45 (m,4), (m,4), 6.72 (d,2) ppm.

Workup

  1. customwas partitioned with ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica gel (50 g) with methylene chloride/hexane (3/1)

Sources & evidence

ORD record
ord-2a565fe2a8114decacccf9a4a905c757
Source dataset
uspto-grants-1999_12
Patent number
US06004981

Reaction notes

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