2-Bromo-3-nitro-5-(trifluoromethyl)pyridine → 3-Nitro-5-(trifluoromethyl)picolinonitrile

HRID 444916Notes

Reaction equation

HRID 444916 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.[Cu][C:16]#[N:17]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N+:8]([C:7]1[C:2]([C:16]#[N:17])=[N:3][CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 463152002-Bromo-3-nitro-5-(trifluoromethyl)pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 453821473-Nitro-5-(trifluoromethyl)picolinonitrile

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-Bromo-3-nitro-5-trifluoromethyl-pyridine (10.00 g, 36.87 mmol) was dissolved in toluene (250 ml) with stirring to give a pale yellow solution. Tetrabutylammonium bromide (11.90 g, 36.9 mmol) was added followed by copper(I) cyanide (9.92 g, 111 mmol) and the mixture was heated at reflux for 10 h. After cooling to RT, the reaction mixture was partitioned between water (750 ml) and EtOAc (750 ml). The organic fractions were combined, washed with water (2×250 ml) and brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford the title product. 1H-NMR: [400 MHz, DMSO-d6 δH 9.55 (1H, m, ArH), 9.24 (1H, m, ArH)

Workup

  1. customto give a pale yellow solution
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 10 h
  4. customthe reaction mixture was partitioned between water (750 ml) and EtOAc (750 ml)
  5. washwashed with water (2×250 ml) and brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1432742050b14b79a454a3a11fc3e088
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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