Sodium Carbonate → 2-(Furan-2-yl)benzaldehyde

Temperature

80 °C

2-Formylphenylboric acid (300 mg, 2.0 mmol), 2-bromofuran obtained in Example 64a (588 mg, 4.0 mmol), and tetrakis triphenylphosphine palladium (15 mg) were dissolved in a mixed solvent of toluene (38 ml) and methanol (5 ml). The solution was added with 2M aqueous sodium carbonate solution (20 ml) and heated at 80° C. with stirring for 6 hours. The reaction mixture was stand for cooling, and then the solvent was evaporated. The mixture was extracted with dichloromethane, and the extract was washed with a mixture of 2M aqueous sodium carbonate solution (10 ml) and aqueous solution of ammonia (2 ml), and dried over sodium sulfate. Insoluble solids were removed by filtration, and the filtrate was evaporated under reduced pressure to obtain the title compound as crude yellow oil (126 mg). The resulting crude product was used in the next reaction without purification.

1. temperaturefor cooling
2. customthe solvent was evaporated
3. extractionThe mixture was extracted with dichloromethane
4. washthe extract was washed with a mixture of 2M aqueous sodium carbonate solution (10 ml) and aqueous solution of ammonia (2 ml)
5. dry with materialdried over sodium sulfate
6. customInsoluble solids were removed by filtration
7. customthe filtrate was evaporated under reduced pressure

ORD record

ord-16a51c3fe97d42e88b2741bd34b72736

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166617B2