Dibromomethane → 1,3-Benzodioxole, 6-bromo-4-methoxy-

To dimethylformamide (400 mL) was added 1-bromo-3,4-dihydroxy-5-methoxybenzene (40 g, 182 mmol), potassium carbonate (75.7 g, 548 mmol), and dibromomethane (95.2 g, 548 mmol), followed by heating to reflux for 1 hour. The solvent was evaporated in vacuo, and the residue was taken up into ethyl ether, filtered, washed with saturated potassium carbonate solution, brine, 1N citric acid solution, and brine. The organic phase was dried over anhydrous magnesium sulfate and filtered through charcoal. The filtrate was concentrated in vacuo giving a crystalline precipitate which was filtered, washed with hexane, and dried in vacuo to a solid. This material was distilled at 2 mm Hg, 125° C., giving a crystalline solid, 21.7 g, 52% yield. NMR spectra and elemental analysis were consistent with the structure.

1. temperatureby heating
2. temperatureto reflux for 1 hour
3. customThe solvent was evaporated in vacuo
4. filtrationfiltered
5. washwashed with saturated potassium carbonate solution, brine, 1N citric acid solution, and brine
6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
7. filtrationfiltered through charcoal
8. concentrationThe filtrate was concentrated in vacuo
9. customgiving a crystalline precipitate which
10. filtrationwas filtered
11. washwashed with hexane
12. customdried in vacuo to a solid
13. distillationThis material was distilled at 2 mm Hg, 125° C.
14. customgiving a crystalline solid, 21.7 g, 52% yield

ORD record

ord-18a8a6ab08d94b40aab339d5a9231f22

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06252070B1