반응 #1606351

반응 방정식

2,2,6,6-tetramethylpiperidine

tert-butyl(2-fluoro-6-methylphenoxy)dimethylsilane

B(O-iPr)3

n-BuLi

→

title compound

(3-((tert-Butyldimethylsilyl)oxy)-2-fluoro-4-methylphenyl)boronic acid

용매

THF

THF

HOAc

water

반응 조건

후처리

1. 1
   workup.ADDITIONTo a 25 mL flask vial were added a stir-bar
2. 2
   온도warmed to 0° Celsius
3. 3
   온도the mixture was re-cooled to −78° Celsius
4. 4
   workup.WAITAfter 15 min
5. 5
   workup.ADDITIONwas added over the course of 6 min
6. 6
   workup.WAITcontinued for 1 hour at −78° Celsius
7. 7
   온도The mixture was then warmed to rt
8. 8
   workup.STIRRINGstirred for 5 min
9. 9
   추출The aqueous mixture was then extracted with EtOAc (3×100 mL)
10. 10
    건조the combined extracts dried over Na2SO4
11. 11
    여과filtered
12. 12
    농축concentrated to dryness

실험 절차

To a 25 mL flask vial were added a stir-bar, 2.1 mL dry THF, and 2,2,6,6-tetramethylpiperidine (0.22 mL, 1.0 mmol). The flask was cooled to −78° Celsius and then treated with n-BuLi (0.48 mL, 1.9 mmol, 2.5 M in hexanes) over 2 minutes. The resultant mixture was stirred for 5 min and then warmed to 0° Celsius. After 30 min, the mixture was re-cooled to −78° Celsius and treated with B(O-iPr)3 (0.26 mL, 1.1 mmol) over 4 min. After 15 min, a solution consisting of tert-butyl(2-fluoro-6-methylphenoxy)dimethylsilane (247 mg, 1.03 mmol) in dry THF (2.1 mL) was added over the course of 6 min and stirring continued for 1 hour at −78° Celsius. The mixture was then warmed to rt, treated with HOAc (0.5 mL), and then poured into water (100 mL) and stirred for 5 min. The aqueous mixture was then extracted with EtOAc (3×100 mL), the combined extracts dried over Na2SO4, filtered, and concentrated to dryness to give the title compound, which was used directly in the next synthetic step.

출처