Reaktion #1269882

Reaktionsgleichung

water

4-bromonicotinaldehyde

phenylboronic acid

Na2CO3

→

4-phenylnicotinaldehyde

Ausbeute 50.5%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with EtOAc
2. 2
   Filtrationthe combined organic layers were filtered (celite)
3. 3
   Trocknendried (MgSO4)
4. 4
   SonstigePurification by flash chromatography (heptane/EtOAc, gradient 5-40% EtOAc)

Vorschrift

4-bromonicotinaldehyde (150 mg, 0.81 mmol), phenylboronic acid (98 mg, 0.81 mmol) and tetrakis(triphenylphosphine)palladium(0) (46.6 mg, 0.05 mmol) were mixed in dioxane (3.5 mL). Na2CO3 (2 M solution in water, 0.81 mL, 1.63 mmol) was added and the reaction mixture was stirred and heated in the microwave (110° C., 150 W) for 30 min. After addition of excess water followed by extraction with EtOAc, the combined organic layers were filtered (celite) and dried (MgSO4). Purification by flash chromatography (heptane/EtOAc, gradient 5-40% EtOAc) provided 4-phenylnicotinaldehyde (75 mg, 48%) as a dark yellow gum. ESI-MS [M+H]+=279.1.

Quelle