Sodium Carbonate → 4'-Dibenzofuran-4-yl-biphenyl-4-carbaldehyde

HRID 1782630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1782630
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]3[O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:23]=3[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.[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>[CH:22]1[C:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[O:25][C:24]=2[C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:6]3[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=3)=[CH:18][CH:17]=2)=[CH:20][CH:21]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 590220984-(4-Bromophenyl)dibenzo[b,d]furan

Produkt 1

HCID 596961794'-Dibenzofuran-4-yl-biphenyl-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4-(4-bromophenyl)-dibenzofuran (from the previous reaction) in toluene (40 mL). Tetrakis-(Triphenylphosphine)-palladium(0) (270 mg, 5 mol %) and 2 N sodium carbonate (4.7 mL, 9.4 mmol) were added and then the reaction was heated to 100° C. (oil bath temp.) for 2-3 h until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with 0.5 N hydrochloric acid, water and sat'd aq NaCl and then dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (10-20% ethyl acetate in heptane) afforded the title compound has a white solid (1.51 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe phases were separated
  4. extractionthe aqueous phase being further extracted with ethyl acetate (2×20 mL)
  5. washThe combined organic extracts were washed with 0.5 N hydrochloric acid, water
  6. dry with materialdried over anhyd MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography (10-20% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-c107263d2030456a86346d5540e75258
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498356B2

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