Tetrahydrofuran → 5-Bromo-3-fluoropyridine-2-carbonitrile

HRID 535900Notes

Reaction equation

HRID 535900 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+]([O-])=O)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[F-:13].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:13])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 441966805-Bromo-3-fluoropyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-bromo-3-nitropicolinonitrile (6.84 g, 30 mmol) in dimethylsulfoxide was cooled to −25° C. and treated with 1M tetra-n-butylammonium fluoride in tetrahydrofuran (60 mL, 60 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. It was quenched with water and extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated to provide crude title compound.

Workup

  1. customIt was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c46db34b922745db8c38683e18eff2ac
Source dataset
uspto-grants-2014_10
Patent number
US08859546B2

Reaction notes

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