Reaktion #987514

Reaktionsgleichung

sodium carbonate

4-formylphenylboronic acid

4-(4-bromophenyl)-dibenzofuran

→

title compound

4′-Dibenzofuran-4-yl-biphenyl-4-carbaldehyde

Lösungsmittel

toluene

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Sonstigepartitioned between water and ethyl acetate
3. 3
   SonstigeThe phases were separated
4. 4
   Extraktionthe aqueous phase being further extracted with ethyl acetate (2×20 mL)
5. 5
   WaschenThe combined organic extracts were washed with 0.5 N hydrochloric acid, water
6. 6
   Trocknendried over anhyd MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigePurification by flash column chromatography (10-20% ethyl acetate in heptane)

Vorschrift

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).

Quelle