反応 #2075716

反応方程式

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

収率 72.3%

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

収率 72.3%

溶媒

THF

THF

tetrahydrofuran

反応条件

後処理

1. 1
   温度to warm toward 0° C. for 1 hour
2. 2
   温度cooled to −10° C. again
3. 3
   温度to warm to ambient temperature
4. 4
   抽出extracted with 1N sodium hydroxide twice
5. 5
   抽出extracted with dichloromethane twice
6. 6
   その他dried
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

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).

出典