2-(4-Bromo-3-nitro-phenyl)-3-(trifluoromethyl)-pyridine → 2-Nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzonitrile

HRID 1791220Notes

Reaction equation

HRID 1791220 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[C:21]([Cu])#[N:22]>CC(N(C)C)=O.CCOC(C)=O>[N+:18]([C:3]1[CH:4]=[C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:7][C:2]=1[C:21]#[N:22])([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 220301962-(4-Bromo-3-nitro-phenyl)-3-(trifluoromethyl)-pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 220300632-Nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(4-bromo-3-nitro-phenyl)-3-(trifluoromethyl)-pyridine (0.55 mmol) in DMA (4 mL) add CuCN (0.60 mmol). Stir the mixture 4 hours at 110° C. Cool to room temperature, dilute with 20 ml of EtOAc, and filter through celite pad. Wash the filtrated with brine, dry over Na2SO4, concentrate under vacuum, and purify by flash chromatography (1:1 hexanes/EtOAc) to give 2-nitro-4(3-trifluoromethyl-pyridin-2-yl)-benzonitrile.

Workup

  1. temperatureCool to room temperature
  2. filtrationfilter through celite pad
  3. washWash the
  4. filtrationfiltrated with brine
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate under vacuum
  7. custompurify by flash chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-d65313b8e7bb46489d82036d77557d52
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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