Reacción #58897

Ecuación de reacción

3,5-dihydroxybenzaldehyde

phenylboronic acid

sodium carbonate

trifluoromethanesulfonic anhydride

→

5-Hydroxy-biphenyl-3-carbaldehyde

Disolventes

pyridine

methylene chloride

DME

water

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe temperature below 5° C
2. 2
   LavadoAfter 10 min the mixture was washed with water
3. 3
   Concentraciónthe organic phase was concentrated under reduced pressure
4. 4
   TemperaturaThe mixture was refluxed for 17 h under Argon
5. 5
   Extracciónextracted with ethyl acetate
6. 6
   OtroPurification by chromatography

Procedimiento

A solution of 3,5-dihydroxybenzaldehyde (14.4 mmol) and pyridine (114 mmol) in methylene chloride (20 ml) was slowly added trifluoromethanesulfonic anhydride (36.2 mmol) keeping the temperature below 5° C. After 10 min the mixture was washed with water and the organic phase was concentrated under reduced pressure. The crude brown crystals (6.4 g—product and pyridine −1:1), phenylboronic acid (13.2 mmol), sodium carbonate (39.6 mmol) and dichlorobis(triphenylphosphine)-palladium (II). (3 mol %) was dissolved in DME (40 ml) and water (20 ml). The mixture was refluxed for 17 h under Argon, cooled to room temperature and extracted with ethyl acetate. Purification by chromatography yielded 5-Hydroxy-biphenyl-3-carbaldehyde

Fuente