Sodium Carbonate → (2-Ethyl-4'-methoxy-1,1'-biphenyl-4-yl)acetonitrile

HRID 2076629Notes

Reaction equation

HRID 2076629 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][C:8]=1[CH2:16][CH3:17])(=O)=O.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:16]([C:8]1[CH:9]=[C:10]([CH2:13][C:14]#[N:15])[CH:11]=[CH:12][C:7]=1[C:25]1[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)[CH3:17]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 860880834-(Cyanomethyl)-2-ethylphenyl trifluoromethanesulfonate

Product 1

HCID 67119130(2-Ethyl-4'-methoxy-1,1'-biphenyl-4-yl)acetonitrileYield 66.3%

Conditions

Temperature
80 °C

Procedure

After toluene (150 ml), ethanol (30 ml) and distilled water (30 ml) were added to 4-(cyanomethyl)-2-ethylphenyl trifluoromethanesulfonate (9.7 g, 33 mmol) obtained in Example (26-2), 4-methoxyphenylboronic acid (5.3 g, 35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (2.7 g, 3.3 mol) and sodium carbonate (10.0 g, 94 mmol), the mixture was stirred at 80° C. for 4 hours. After the reaction mixture was cooled to room temperature, the insolubles were removed by filtration. The obtained filtrate was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=7/1-6/1) to give (2-ethyl-4′-methoxy-1,1′-biphenyl-4-yl)acetonitrile as an oil (5.5 g, yield: 66%).

Workup

  1. distillationAfter toluene (150 ml), ethanol (30 ml) and distilled water (30 ml)
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customthe insolubles were removed by filtration
  4. additionThe obtained filtrate was poured into water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was successively washed with water
  7. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  8. customThe residue obtained
  9. customby removing the solvent under reduced pressure
  10. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=7/1-6/1)

Sources & evidence

ORD record
ord-317b4849aa174d758edea0d47abf949f
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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