Reaktion #61755

Reaktionsgleichung

4-Phenyl-pyridine-2-carbaldehyde

propionitrile

trimethylsilyl bromide

NaOH

→

2-bromo-4-phenyl pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting orange suspension was microwaved in a sealed tube at 150° C. for 10 min
2. 2
   workup.ADDITIONcontaining ice
3. 3
   ExtraktionThe aqueous layer was extracted with diethyl ether (2×)
4. 4
   WaschenThe combined organic layers were washed with sat. NaHCO3, brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

4-Phenyl-pyridine-2-carbaldehyde: To a clear, colorless solution of 1A (0.850 g, 4.5 mmol) in propionitrile (4.5 mmol) was added trimethylsilyl bromide (2.95 mL, 22.4 mmol). The resulting orange suspension was microwaved in a sealed tube at 150° C. for 10 min. The reaction was cooled to rt and poured into 1.0 N NaOH containing ice. The aqueous layer was extracted with diethyl ether (2×). The combined organic layers were washed with sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give 1.07 g of 2-bromo-4-phenyl pyridine as an off-white solid. MS 233.9 (M+H)+ and 235.9 (M+2+H)+.

Quelle