تفاعل #1994290

معادلة التفاعل

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

1,2-difluoro-3-methylbenzene

n-butyllithium

diisopropylamine

→

title compound

المردود 50.5%

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

المردود 50.5%

المذيبات

THF

THF

ether

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to −78° C
2. 2
   workup.STIRRINGstirred at −78° C. for 2 h
3. 3
   درجة الحرارةthe brown solution was slowly warmed to 23° C. over 16 hours
4. 4
   استخلاصextracted with water and with 0.1N sodium hydroxide
5. 5
   استخلاصthen extracted with dichloromethane
6. 6
   أخرىThe organic phase was dried
7. 7
   تركيزconcentrated

الإجراء التجريبي

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).

المصدر