تفاعل #614839

معادلة التفاعل

sec-BuLi

2,2-Difluoro-1,3-benzodioxole

H2O2

NaOH

Trimethylborate

→

title compound

المردود 95.3%

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

المردود 95.3%

المذيبات

cyclohexane

cyclohexane

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added drop wise
2. 2
   درجة الحرارةto warm slowly to room temperature
3. 3
   workup.STIRRINGthe reaction mixture stirred for 18 hours at room temperature
4. 4
   أخرىThe reaction was quenched with a 2N aqueous solution of HCl
5. 5
   workup.ADDITIONdiluted with ethyl acetate
6. 6
   أخرىTwo phases were separated
7. 7
   غسيلthe organic layer was washed twice with brine
8. 8
   تجفيفdried over Na2SO4
9. 9
   أخرىevaporated to dryness

الإجراء التجريبي

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).

المصدر