Benzene → 3-(Biphenyl-4-yl)furan

HRID 2299913Notes

Reaction equation

HRID 2299913 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) and a solution of 4-biphenylboronic acid (6.36 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. 1H NMR: δ 8.28 (s, 1H), 7.64-7.55 (m, 6H), 7.50 (s, 1H), 7.45 (t, 2H, J=7.35 Hz), 7.40 (t, 1H, J=7.35 Hz, 6.75 (s, 1H), Anal. calculated for C16H12O: C, 87.25; H, 5.49. Found: C, 87.15; H, 5.52.

Workup

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

Sources & evidence

ORD record
ord-5f19f023a16e45e9a0e41d8cb3fa1b20
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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