반응 #888

반응 방정식

1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

KBr

→

2,5-bis(4-Bromophenyl)-3-(p-tolyloxy)furan

용매

phosphorus trichloride

반응 조건

후처리

1. 1
   온도under reflux for 3-4 hr (TLC followed)
2. 2
   기타The excess PCl3 was removed by distillation
3. 3
   기타the residue was triturated with ice/water (exothermic reaction)
4. 4
   추출The solution was extracted with dichloromethane (75 ml)
5. 5
   세척the dichloromethane layer was washed with saturated sodium bicarbonate solution, water
6. 6
   기타dried (Na2 SO4)
7. 7
   기타The solvent was removed under reduced pressure
8. 8
   기타The residual solid was chromatographed over silica gel
9. 9
   기타An off white crystalline solid was obtained

실험 절차

A solution of 5.0 g (0.01 mole) 1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene in 10 ml phosphorus trichloride was heated under reflux for 3-4 hr (TLC followed). The excess PCl3 was removed by distillation and the residue was triturated with ice/water (exothermic reaction). The solution was extracted with dichloromethane (75 ml) and the dichloromethane layer was washed with saturated sodium bicarbonate solution, water, and dried (Na2 SO4). The solvent was removed under reduced pressure. The residual solid was chromatographed over silica gel using ether:hexane (2:8 to 1:1) as eluant. An off white crystalline solid was obtained, 2.78 g (56%), mp 92°-3° C. IR (KBr) 2923, 2851, 1560, 1506, 1467, 1390, 1209, 1072, 1066, 945, 825, 707, 486. 1H NMR (CDCl3 /35° C.) 7.69 (d, 2H, J=8.8), 7.46-7.43 (m, 6H), 7.12 (d, 2H, J=8.3), 7.0 (d, 2H, J=8.3), 6.47 (s, 1H), 2.31 (s, 3H). 13C NMR (CDCl3 /135° C.) 150.8, 150.1, 142.8, 139.3, 133.0, 131.9, 131.7, 130.3, 129.1, 128.6, 125.1, 125.0, 121.8, 120.5, 117.1, 102.7, 20.6. MS m/e 484 (M+).

출처