Sodium Carbonate → HCID 18448471, compound

Participants

Reaction Steps

2-Nitro-4-bromotoluene (8.74 g, 40.46 mmol) was dissolved in 75 mL dioxane and 25 mL water to which was added diethyl-(3-pyridyl)borane (5.95 g, 40.46 mmol), sodium carbonate (8.58 g, 80.91 mmol) and tetrakis(triphenylphosphine palladium(0) (0.94 g, 0.81 mmol). The mixture was heated at reflux for 18 h then cooled to ambient temperature. The mixture was diluted with 600 mL water and extracted with diethyl ether (2×300 mL). The organic phases were combined and extracted with 0.3 N HCl (3×200 mL). The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (2×300 mL) and the extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 6.39 g (74%) of 2-nitro-4-(3-pyridyl)toluene as a brown oil.

Provenance & Evidence