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

HRID 574225Notes

Reaction equation

HRID 574225 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 9 hrs. 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] δ 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 9 hrs
  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-e37005cfbb0349cdb62cc90ede3467a0
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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