반응 #2328194

반응 방정식

water

1-bromo-3-ethynylbenzene

DMF

4-iodo(difluoromethoxy)benzene

→

1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene

용매

EtOAc

반응 조건

후처리

1. 1
   온도The reaction mixture became warm
2. 2
   workup.ADDITIONafter the addition
3. 3
   기타The aqueous layer was separated
4. 4
   추출extracted twice with EtOAc
5. 5
   건조The combined organic layers were dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated onto 40 g Celite
8. 8
   기타Flash chromatography (SiO2, Hexanes) provided 12 g, 92%
9. 9
   기타of the title compound as a yellow oil that crystallized into a yellow solid

실험 절차

To a mixture of 1-bromo-3-ethynylbenzene (9.1 g, 50.26 mmol), TEA (22.38 g, 30.8 mL, 221.1 mmol), PdCl2(ACN)2 (1.41 g, 2.01 mmol) and DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol). The reaction mixture became warm after the addition was completed. The mixture was stirred for 4 h. Then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 40 g Celite. Flash chromatography (SiO2, Hexanes) provided 12 g, 92%, of the title compound as a yellow oil that crystallized into a yellow solid upon standing.

출처