Benzene → 3-(Biphenyl-4-yl)furan

HRID 382127Notes

Reaction equation

HRID 382127 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].[C:19]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>CCO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:19]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:24]=[CH:23][C:22]([C:2]2[CH:6]=[CH:5][O:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 891643-BromofuranHCID 1512531,1'-Biphenyl-4-yl-boronic acid

Product 1

HCID 183802933-(Biphenyl-4-yl)furanYield 76%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A biphasic mixture of 3-bromofuran (2.90 mL, 32.1 mmol), benzene (70 mL), and 2N aqueous Na2CO3 (50 mL) was degassed and purged with argon. Tetrakis(triphenylphosphine) palladium(0) (3.7 g, 3.2 mmol) arid a solution of 4-biphenylboronic acid (6.3 g, 32.1 mmol) in EtOH (50 mL) were added sequentially. The mixture was heated at 80° C. for 18 hours, allowed to cool, and partitioned between CH2Cl2 and H2O. The aqueous layer was separated and extracted with CH2Cl2 two times. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to a crude product, which was dissolved in a minimal amount of CH2Cl2 and applied to a flash chromatography column packed with hexanes. Elution with 10% CH2Cl2/hex led to some mixed fractions, which were rechromatographed. A total of 5.37 g (76%) of 3-(biphenyl-4-yl)furan was obtained as a pale yellow oil.

Workup

  1. customwas degassed
  2. custompurged with argon
  3. additionwere added sequentially
  4. temperatureto cool
  5. custompartitioned between CH2Cl2 and H2O
  6. customThe aqueous layer was separated
  7. extractionextracted with CH2Cl2 two times
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated to a crude product, which
  11. dissolutionwas dissolved in a minimal amount of CH2Cl2
  12. washElution with 10% CH2Cl2/hex
  13. customwere rechromatographed

Sources & evidence

ORD record
ord-da12ee5354e847e8beb2d47e19e329f0
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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