반응 #2515331

반응 방정식

water

(5-bromo-2-chloro-benzyl)-cyclopropyl-carbamic acid tert-butyl ester

K2CO3

water

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

→

title compound

수율 79.0%

(2-Chloro-5-vinyl-benzyl)-cyclopropyl-carbamic Acid tert-butyl Ester

수율 79.0%

용매

DME

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 3 h
3. 3
   온도to cool to rt
4. 4
   추출The mixture was extracted with Et2O (4×)
5. 5
   건조extracts were dried over MgSO4
6. 6
   여과filtered
7. 7
   기타the solvents were removed under reduced pressure
8. 8
   기타Purification of the crude by FC (heptane/EtOAc 9:1)

실험 절차

To a sol. of (5-bromo-2-chloro-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (105 g, 0.292 mol) in DME (800 mL) under N2 at rt was added Pd(PPh3)4 (16.9 g, 14.6 mmol). The mixture was stirred at rt for 30 min, and K2CO3 (40.7 g, 292 mmol), water (350 mL) and 4,4,5,5-tetramethyl-2-vinyl-[1,3,2]dioxaborolane (52.0 mL, 292 mmol) were added. The mixture was heated to reflux for 3 h. The mixture was allowed to cool to rt, and water (500 mL) was added. The mixture was extracted with Et2O (4×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 9:1) yielded the title compound (70.9 g, 79%). LC-MS: tR=1.10 min; ES+: 293.38.

출처