Methyl iodide → (2,2-Difluoro-7-methyl-1,3-benzodioxol-4-yl)boronic acid

Temperature

-78 °C

(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.

1. additionwas added dropwise
2. stirringthe reaction mixture was stirred for 2 hours while the temperature
3. customto reach room temperature
4. customThe reaction was quenched by addition of an aqueous 2N solution of HCl
5. additiondiluted with ethyl acetate
6. customThe organic layer was collected
7. washwashed twice with brine
8. dry with materialdried over Na2SO4
9. customevaporated to dryness
10. customCrystallization from n-heptane

ORD record

ord-d2f505d1d255450a8c5eb99f499f23f2

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346790B2