Sodium Carbonate → 4-Methoxy-3-(thiophen-2-yl)benzaldehyde

Tetrakis(triphenylphosphine)palladium(0) (0.24 g, 0.21 mmol) was added to a solution of 4-methoxy-3-bromobenzaldehyde (1.5 g, 6.98 mmol) in toluene (15 mL) and ethanol (15 mL), followed by a 2 M aqueous solution of sodium carbonate (14 mL, 28 mmol). To this mixture was added thiophene-2-boronic acid (0.98 g, 7.68 mmol), and the mixture was heated to reflux. After 3 hours, the reaction was partitioned between water (100 mL) and ethyl acetate (250 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (75 mL) and brine (75 mL), dried with magnesium sulfate and concentrated. Chromatography (silica, 20% ethyl acetate/hexanes) afforded 1.3 g (87%) of 4-methoxy-3-thiophen-2-yl-benzaldehyde as a yellow oil.

1. temperaturethe mixture was heated to reflux
2. customthe reaction was partitioned between water (100 mL) and ethyl acetate (250 mL)
3. washThe organic layer was washed with saturated aqueous sodium bicarbonate (75 mL) and brine (75 mL)
4. dry with materialdried with magnesium sulfate
5. concentrationconcentrated

ORD-Eintrag

ord-6f61e9f503924afaa8e686c132437d02

Quelldatensatz

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06689806B1