Реакция #2075716

Уравнение реакции

2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

isopropyl-magnesium chloride

1-Bromo-4-chloro-2,5-difluorobenzene

diethyl ether

→

title compound

Выход 72.3%

2-(4-Chloro-2,5-difluorophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Выход 72.3%

Растворители

THF

THF

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураto warm toward 0° C. for 1 hour
2. 2
   Температураcooled to −10° C. again
3. 3
   Температураto warm to ambient temperature
4. 4
   Экстракцияextracted with 1N sodium hydroxide twice
5. 5
   Экстракцияextracted with dichloromethane twice
6. 6
   Другоеdried
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated

Методика

1-Bromo-4-chloro-2,5-difluorobenzene (1.11 g, 4.9 mmol) was dissolved in tetrahydrofuran (THF; 15 mL) and cooled to −10° C. A 2.0M solution of isopropyl-magnesium chloride (2.7 mL, 5.4 mmol) in THF was added dropwise via a syringe. The reaction mixture was stirred at −10° C. for 1 hour, allowed to warm toward 0° C. for 1 hour, then cooled to −10° C. again. A solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.0 g, 5.4 mmol) in THF (1.0 mL) was then added dropwise and the reaction was allowed to warm to ambient temperature. The reaction mixture was then added to diethyl ether and extracted with 1N sodium hydroxide twice. The aqueous phases were combined, acidified to pH 3 with concentrated HCl, and extracted with dichloromethane twice. The organic phases were combined, dried, filtered and concentrated to give the title compound (0.97 g, 72.3% yield) that was used without further purification: 1H NMR (CDCl3): δ 7.45 (dd, 1H), 7.09 dd, 1H), 1.36 (s, 12H).

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