تفاعل #614837

معادلة التفاعل

(2,2-difluoro-1,3-benzodioxol-4-yl)boronic acid

Intermediate 195

(2,2-difluoro-1,3-benzodioxol-4-yl)boronic acid

sec-BuLi

cyclohexane

Methyl iodide

→

title compound

(2,2-difluoro-7-methyl-1,3-benzodioxol-4-yl)boronic acid

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGthe reaction mixture was stirred for 2 hours while the temperature
3. 3
   أخرىto reach room temperature
4. 4
   أخرىThe reaction was quenched by addition of an aqueous 2N solution of HCl
5. 5
   workup.ADDITIONdiluted with ethyl acetate
6. 6
   أخرىThe organic layer was collected
7. 7
   غسيلwashed twice with brine
8. 8
   تجفيفdried over Na2SO4
9. 9
   أخرىevaporated to dryness
10. 10
    أخرىCrystallization from n-heptane

الإجراء التجريبي

(2,2-difluoro-1,3-benzodioxol-4-yl)boronic acid (Intermediate 195, crude material) was dissolved in THF (20 mL) and the resulting solution cooled down to −78° C. sec-BuLi 1.4M solution in cyclohexane (17.4 ml, 24.36 mmol) was added dropwise and the reaction mixture was stirred for 1.5 hours at −78° C. Methyl iodide (4.6 ml, 73 mmol) was then added and the reaction mixture was stirred for 2 hours while the temperature was allowed to reach room temperature. The reaction was quenched by addition of an aqueous 2N solution of HCl and diluted with ethyl acetate. The organic layer was collected and then washed twice with brine, dried over Na2SO4 and evaporated to dryness. Crystallization from n-heptane afforded the title compound (150 mg) as white solid.

المصدر