Hydrogen Peroxide → 2,2-Difluoro-1,3-benzodioxol-4-ol

Temperatur

-78 °C

2,2-Difluoro-1,3-benzodioxole (320 mg, 2.05 mmol) was dissolved in THF (2.5 mL) and cyclohexane (1.2 mL) and the resulting solution cooled down to −78° C. sec-BuLi 2M solution in cyclohexane (1.025 ml, 2.05 mmol) was added drop wise and the reaction mixture stirred for 2 hours at −78° C. Trimethylborate (230 mg, 2.25 mmol) was added and the mixture was allowed to warm slowly to room temperature. A 30% w/w aqueous solution of H2O2 (4.1 mmol) and NaOH (82 mg, 2.05 mmol) were added and the reaction mixture stirred for 18 hours at room temperature. The reaction was quenched with a 2N aqueous solution of HCl and diluted with ethyl acetate. Two phases were separated and the organic layer was washed twice with brine, dried over Na2SO4 and evaporated to dryness, affording the title compound (340 mg).

1. additionwas added drop wise
2. temperatureto warm slowly to room temperature
3. stirringthe reaction mixture stirred for 18 hours at room temperature
4. customThe reaction was quenched with a 2N aqueous solution of HCl
5. additiondiluted with ethyl acetate
6. customTwo phases were separated
7. washthe organic layer was washed twice with brine
8. dry with materialdried over Na2SO4
9. customevaporated to dryness

ORD-Eintrag

ord-83b7b301ea65407dbc620c3fc0d63a85

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09346790B2