Sodium Carbonate → 5-(Furan-2-yl)-2,3-dimethoxybenzonitrile

HRID 56515Notes

Reaction equation

HRID 56515 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734357Furan-2-boronic acidHCID 226838165-Bromo-2,3-dimethoxybenzonitrile

Product 1

HCID 584320135-(Furan-2-yl)-2,3-dimethoxybenzonitrileYield 94%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-bromo-2,3-dimethoxybenzonitrile (0.958 g, 4.0 mmol), 2-furylboronic acid (0.53 g, 4.7 mmol), dioxane (24 mL), H2O (8 mL) and Na2CO3 (1.1 g, 10.4 mmol) was added tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol). The mixture was degassed by alternately putting under house vacuum and argon three times for several minutes each then heated at 85° C. under argon for 16.5 hrs. After cooling to room temperature, the mixture was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-20% EtOAc-hexanes) provided 5-(furan-2-yl)-2,3-dimethoxybenzonitrile as a white solid (0.85 g, 94% yield).

Workup

  1. customThe mixture was degassed
  2. waitby alternately putting under house vacuum and argon three times for several minutes
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with H2O
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography (0-20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-49250adb226a444ab760551ad394d451
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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