반응 #2328164

반응 방정식

EtOAc

3-bromophenylacetylene

4-iodo(difluoromethoxy)benzene

water

→

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

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction mixture had gotten 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 over 40 g Celite
8. 8
   기타Flash chromatography (SiO2, Hexanes) gave 12 g, 92%
9. 9
   기타of the title compound as a yellow oil that had crystallized into a solid

실험 절차

To a solution of 3-bromophenylacetylene (9.1 g, 50.26 mmol), TEA (22.4 g, 221 mmol, 30.8 mL), bis(triphenylphosphine)dichloropalladium(II) (1.41 g, 2.01 mmol), and CuI (230 mg, 1.2 mmol) in DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol) at room temperature. The reaction mixture had gotten warm after the addition was completed. The mixture was stirred for 4 h then the mixture was portioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated over 40 g Celite. Flash chromatography (SiO2, Hexanes) gave 12 g, 92%, of the title compound as a yellow oil that had crystallized into a solid after being undisturbed for 3d. 1H NMR 500 MHz (DMSO-d6) δ 7.34 (dt, 2H, J=8.92 Hz, 4.70 Hz); 7.42 (t, 1H, 72.99 Hz); 7.54 (t, 1H, J=7.88 Hz); 7.85-7.88 (m, 1H); 7.94-7.97 (m, 1H); 8.00 (dt, 1H, J=8.93 Hz, 4.87 Hz); 8.04 (t, 1H, J=1.80 Hz).

출처