Acetonitrile → 2-Fluoro-5-nitropyridine

HRID 2185716Notes

Reaction equation

HRID 2185716 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F-:11].[K+].C(#N)C>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>[F:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 783082-Chloro-5-nitropyridine2×HCID 522689Potassium Fluoride

Product 1

HCID 952642-Fluoro-5-nitropyridineYield 54%

Reagents, catalysts & solvents 2

HCID 2724163Tetraphenylphosphonium BromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

2-Chloro-5-nitropyridine (100 g, 0.656 mol, Aldrich), potassium fluoride (84.1 g, 1.45 mol, Aldrich), tetraphenylphosphonium bromide (95.3 g, 0.227 mol, Aldrich), and acetonitrile (1.5 L) were combined and heated at reflux until consumption of the 2-chloro-5-nitropyridine was complete. The volume of the mixture was reduced to 750 mL, diluted with 2 L of ether, filtered and concentrated. The resultant residue was triturated with hot hexane, and the combined hexane extracts were concentrated to give of the title compound (48 g, 54%): 1H NMR (CDCl3, 300 MHz) δ7.15 (dd, J=3, 6 Hz, 1H), 8.64 (m, 1H), 9.15 (d, J=1.6 Hz, 1H).

Workup

  1. temperatureheated
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe resultant residue was triturated with hot hexane
  5. concentrationthe combined hexane extracts were concentrated

Sources & evidence

ORD record
ord-4e0711f6257042ec9b138ef7484f8a9e
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

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