Dimethylformamide → HCID 66643957, compound

Participants

Reaction Conditions

Reaction Steps

To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 minutes and then heated to 145° C. to obtain a homogeneous solution. The solution was aged at 145° C. for 2 hours, and then the reaction mixture was cooled to 95° C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 hours. The reaction was cooled to room temperature, the solids filtered through Solka-Flok® powdered cellulose and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through Solka-Flok® and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5% brine solution (3×500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgSO4, filtered and evaporated. The solids were slurried in 250 mL MTBE at room temperature, and then filtered and washed with 100 mL MTBE. The solids were dried under vacuum at room temperature, providing 5-hydroxy-4-methyl-3H-isobenzofuran-1-one.

Provenance & Evidence