Pivalic acid → 2-Nitrodibenzofuran

Participants

Reaction Conditions

Reaction Steps

In a 1 L round-bottom flask, 1-nitro-4-phenoxybenzene (50 g, 232 mmol), potassium carbonate (3.21 g, 23.23 mmol), palladium acetate (2.61 g, 11.62 mmol), and 280 mL of pivalic acid were added. The mixture was heated to 120° C. in air. After 3 days the reaction mixture was cooled in an ice bath. 125 mL of 50% sodium hydroxide solution was added slowly in portions over time. The black emulsion was diluted with a large amount of water and ethyl acetate, filtered through Celite. The organic layer was separated, dried over magnesium sulfate, and filtered. The solvent was evaporated and pre-adsorbed onto Celite. The Celite mixture was purified by silica gel plug eluting with 10% to 50% dichloromethane in hexanes. 36.4 g (63% yield) desired product was obtained.

Provenance & Evidence