Dimethylformamide → HCID 66643957, compound

Temperature

145 °C

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.

1. customThe solution was sparged with N2 for 15 minutes
2. customto obtain a homogeneous solution
3. temperaturethe reaction mixture was cooled to 95° C
4. custom(sparged with N2)
5. waitthe reaction aged for 20 hours
6. temperatureThe reaction was cooled to room temperature
7. filtrationthe solids filtered through Solka-Flok®
8. washthe cake washed with 50 mL DMF
9. additionTo a 3 L flask containing 1 L EtOAc
10. additionwas added the DMF filtrate
11. customA precipitate coating formed in bottom of flask
12. filtrationThe DMF/EtOAc suspension was filtered through Solka-Flok®
13. washthe cake was washed with 250 mL EtOAc
14. washThe resulting filtrate was washed with 5% brine solution (3×500 mL)
15. extractionThe aqueous layers were extracted with 500 mL EtOAc
16. dry with materialthe combined organics were dried over MgSO4
17. filtrationfiltered
18. customevaporated
19. customwere slurried in 250 mL MTBE at room temperature
20. filtrationfiltered
21. washwashed with 100 mL MTBE
22. customThe solids were dried under vacuum at room temperature

ORD record

ord-76dc189732474ddab4d966bef3033ef9

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108947B2