반응 #1514898

반응 방정식

4-bromo-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene

4-tert-butylphenylboronic acid

K3PO4

dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine

→

4-(4-tert-Butylphenyl)-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene

용매

water

toluene

반응 조건

후처리

1. 1
   온도The resulting mixture was cooled to room temperature
2. 2
   기타The organic layer was separated
3. 3
   추출the aqueous layer was extracted with 3×100 ml of dichloromethane
4. 4
   추출The combined organic extract
5. 5
   건조was dried over Na2SO4
6. 6
   기타evaporated to dryness
7. 7
   기타The target product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes)

실험 절차

In argon atmosphere, a mixture of 34.6 g (105 mmol) of 4-bromo-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene, 22.4 g (126 mmol) 4-tert-butylphenylboronic acid, 66.8 g (315 mmol) of K3PO4, 1.21 g (21 mmol) of Pd(dba)2, 1.73 g (42 mmol) of dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine and 350 ml of toluene was stirred for 12 h at 100° C. The resulting mixture was cooled to room temperature, and then 600 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 3×100 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. The target product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes). Yield 24.0 g (62%).

출처