Sodium Carbonate → 3-(Pyridin-3-yl)phenol

Participants

Reaction Steps

3-bromophenol (49.42 g, 285.66 mmol) and diethyl-(3-pyridyl)borane (40.00 g, 272.05 mmol) were dissolved in 945 mL of a 4:2:1 mixture of THF/H2O/ethanol in a 2 L round bottom flask equipped with a magnetic stirrer. Sodium carbonate (57.7 g, 544.11 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.14 g, 2.72 mmol) was added and the mixture was heated at reflux for 2 h then cooled to ambient temperature and stirred an additional 18 h. The mixture was diluted with 400 mL water and extracted with ethyl acetate (3×500 mL). The organic phases were combined and dried over anhydrous sodium sulfate, filtered and concentrated to a volume of 1 L. The organic solution was diluted with 500 mL water and made acidic with 12N HCl. The layers were separated and the organic phase extracted with water (2×300 mL). The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (3×500 mL) and the extracts were combined, washed with 500 mL brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 40.91 g (88%) of 3-(3-hydroxyphenyl)pyridine as a pale yellow oil which crystallized on standing.

Provenance & Evidence