Sodium Hydroxide → 5-Benzo[1,3]dioxol-5-yl-4-bromo-oxazole

Temperature

-78 °C

To a −78° C. solution of 5-benzo[1,3]dioxol-5-yl-oxazole (670 mg, 3.54 mmol) in dimethylformamide (5 mL) was slowly added lithium bis(trimethylsilyl)amide(3.54 mL, 1 M in THF, 3.54 mmol, 1 equiv). The reaction mixture was stirred under nitrogen atmosphere for 1 hour at −78° C., and then treated slowly with a solution of N-bromosuccinamide (630 mg, 3.54 mmol, 1 equiv) in dimethylformamide (2 mL). The resulting reaction mixture was stirred at −78° C. for 1 hour, warmed to ambient temperature and poured into a mixture methylene chloride and 1 N aqueous sodium hydroxide. The aqueous layer was exctracted with methylene chloride, and the combined organics were washed with 1 N aqueous sodium hydroxide and brine, then dried over magnesium sulfate and concentrated in vacuo to provide 5-benzo[1,3]dioxol-5-yl-4-bromo-oxazole (853 mg, 90%).

1. customTo a −78° C.
2. customThe resulting reaction mixture
3. stirringwas stirred at −78° C. for 1 hour
4. temperaturewarmed to ambient temperature
5. washthe combined organics were washed with 1 N aqueous sodium hydroxide and brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo

ORD record

ord-7cd803ba680441adb25e2eec70f74962

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07273936B2