Potassium Carbonate → 4-[(4-Fluorophenyl)methoxy]-3-nitropyridine

HRID 1988829Notes

Reaction equation

HRID 1988829 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].COCCOCCN(CCOCCOC)CCOCCOC>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:17][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 680224-Fluorobenzylic alcoholHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 687034164-[(4-Fluorophenyl)methoxy]-3-nitropyridineYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-3-nitropyridine (2.0 g, 12.62 mmol) prepared in Step 1 of Preparation 1 was added to a suspension of 4-fluorobenzyl alcohol (2.04 ml, 18.92 mmol), potassium carbonate (1.74 g, 12.62 mmol), and potassium hydroxide (2.38 g, 50.48 mmol) in anhydrous toluene (100 ml). A catalytic amount of tris[2-(2-methoxyethoxy)ethyl]amine was added to the reaction mixture, which was then stirred for 1 hour at room temperature. The reaction mixture was filtered and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, (v/v)) to give the titled compound as a white solid (2.5 g, 86.3%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, (v/v))

Sources & evidence

ORD record
ord-6bb0bbb85b0946319ed56200dc5d8de6
Source dataset
uspto-grants-2010_01
Patent number
US07642269B2

Reaction notes

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