反応 #614839

反応方程式

sec-BuLi

2,2-Difluoro-1,3-benzodioxole

H2O2

NaOH

Trimethylborate

→

title compound

収率 95.3%

2,2-difluoro-1,3-benzodioxol-4-ol

収率 95.3%

溶媒

cyclohexane

cyclohexane

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added drop wise
2. 2
   温度to warm slowly to room temperature
3. 3
   workup.STIRRINGthe reaction mixture stirred for 18 hours at room temperature
4. 4
   その他The reaction was quenched with a 2N aqueous solution of HCl
5. 5
   workup.ADDITIONdiluted with ethyl acetate
6. 6
   その他Two phases were separated
7. 7
   洗浄the organic layer was washed twice with brine
8. 8
   乾燥dried over Na2SO4
9. 9
   その他evaporated to dryness

実験手順

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).

出典