Hydrochloric Acid → HCID 11127172, compound

Temperature

-78 °C

To tetrahydrofuran (40 mL) was added magnesium turnings (2.33 g, 95.8 mmol), 1-bromo-3,4-methylenedioxy-5-methoxybenzene (21.7 g, 93.9 mmol) and a catalytic amount of iodine. Following vigorous reaction, the metal was consumed, and the solution was added to a solution of trimethylborate (38 mL, 334 mmol) in tetrahydrofuran (100 mL) at −78° C. over 45 minutes. The mixture was stirred at −78° C. for an additional 2 hours, then at 25° C. overnight. To the mixture was added 1N HCl (200 mL) followed by stirring at 25° C. for 3 days. The solvent was removed in vacuo, and the suspension was extracted with ethyl ether. The ether phase was washed with brine, and the product was extracted into 0.5N NaOH. The NaOH solution was washed with ethyl ether and acidified to pH 1 with 2N HCl. The acidified aqueous phase was extracted with ethyl ether, washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to a brown solid, 7.43 g, 40% yield. The material was of sufficient purity to be used in subsequent preparations.

1. customreaction
2. customthe metal was consumed
3. customat 25° C.
4. customovernight
5. stirringby stirring at 25° C. for 3 days
6. customThe solvent was removed in vacuo
7. extractionthe suspension was extracted with ethyl ether
8. washThe ether phase was washed with brine
9. extractionthe product was extracted into 0.5N NaOH
10. washThe NaOH solution was washed with ethyl ether
11. extractionThe acidified aqueous phase was extracted with ethyl ether
12. washwashed with brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltered
15. customevaporated to a brown solid, 7.43 g, 40% yield

ORD record

ord-883d2a366c2c4190b3df360851183380

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06545150B2