반응 #1994290

반응 방정식

2-Isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

1,2-difluoro-3-methylbenzene

n-butyllithium

diisopropylamine

→

title compound

수율 50.5%

2-(2,3-Difluoro-4-methylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

수율 50.5%

용매

THF

THF

ether

THF

반응 조건

후처리

1. 1
   온도cooled to −78° C
2. 2
   workup.STIRRINGstirred at −78° C. for 2 h
3. 3
   온도the brown solution was slowly warmed to 23° C. over 16 hours
4. 4
   추출extracted with water and with 0.1N sodium hydroxide
5. 5
   추출then extracted with dichloromethane
6. 6
   기타The organic phase was dried
7. 7
   농축concentrated

실험 절차

A 2.5 M solution of n-butyllithium (3.4 mL, 8.5 mmol) was added to a stirred solution of diisopropylamine (1.2 mL, 8.5 mmol) in THF (25 mL) at −20° C. The resulting solution was stirred at −20° C. for 10 minutes, then cooled to −78° C. A solution of 1,2-difluoro-3-methylbenzene (1.0 g, 7.8 mmol) in THF was added dropwise and stirred at −78° C. for 2 h. 2-Isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (1.6 g, 8.6 mmol) in THF was then added and the brown solution was slowly warmed to 23° C. over 16 hours. The reaction mixture was then added to ether and extracted with water and with 0.1N sodium hydroxide. The combined aqueous extracts were acidified with concentrated HCl then extracted with dichloromethane. The organic phase was dried and concentrated to give the title compound (1.0 g, 50% yield): 1H NMR (CDCl3): δ 7.32 (m, 1H), 6.92 (m, 1H), 2.31 (s, 3H), 1.32 (s, 12H).

출처