Sodium Carbonate → 4-(5-Formylfuran-2-yl)-2-(trifluoromethyl)benzonitrile

HRID 872571Notes

Reaction equation

HRID 872571 reaction equation
[CH:1]([C:3]1[O:7][CH:6]=[C:5](B(O)O)[CH:4]=1)=[O:2].C(=O)([O-])[O-].[Na+].[Na+].Br[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:19]=1>C(O)C.[Pd]>[CH:1]([C:3]1[O:7][C:6]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([C:26]([F:27])([F:29])[F:28])[CH:19]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 52210965-Formylfuran-3-boronic acidHCID 223378254-Bromo-2-(trifluoromethyl)benzonitrile

Product 1

HCID 866702424-(5-Formylfuran-2-yl)-2-(trifluoromethyl)benzonitrileYield 396.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

To the stirred solution of 5-formylfuran-3-boronic acid (0.31 g, 2.2 mmol), palladium (10%) in carbon (0.090 g) and sodium carbonate (0.85 g, 8.0 mmol) in ethanol (10 ml) was added a solution of 4-bromo-2-(trifluoromethyl)benzonitrile (0.50 g, 0.19 mmol) in ethanol (10 ml) under nitrogen atmosphere. The reaction mixture was refluxed for two hours, and then cooled to RT and diluted with ethanol. The mixture was filtered through a pad of Celite, washed with ethanol and the filtrate was evaporated to dryness. Combiflash purification using heptane/ethyl acetate as eluent system afforded 0.20 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.73 (d, 1H), 7.76 (d, 1H), 8.31 (m, 1H), 8.33 (m, 1H), 8.39 (m, 1H), 9.71 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for two hours
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washwashed with ethanol
  4. customthe filtrate was evaporated to dryness
  5. customCombiflash purification

Sources & evidence

ORD record
ord-64f18121f40c4df9b2d758c42fda2bc0
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…