反応 #470974

反応方程式

water

Methyl 5-bromonicotinate

3-trifluoromethylbenzeneboronic acid

K3PO4

→

methyl 5-[3-(trifluoromethyl)phenyl]nicotinate

収率 86.8%

溶媒

EtOAc

dioxane

反応条件

後処理

1. 1
   温度the mixture was cooled to room temperature
2. 2
   ろ過The insoluble material was filtered off
3. 3
   洗浄washed with EtOAc
4. 4
   workup.ADDITIONThe filtrate was poured into saturated aqueous solution of NaHCO3
5. 5
   抽出extracted with EtOAc
6. 6
   洗浄The extract was washed with brine
7. 7
   乾燥dried over MgSO4
8. 8
   濃縮concentrated
9. 9
   その他The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=94/6˜50/50)

実験手順

Methyl 5-bromonicotinate (168.2 mg), 3-trifluoromethylbenzeneboronic acid (165.6 mg), K3PO4 (378.5 mg) and Pd(PPh3)4 (92.2 mg) was mixed in dioxane (5 ml). To the suspension was added water (0.25 ml). And the mixture was heated to 100° C. under stirring. After 6 hours, the mixture was cooled to room temperature and was diluted with EtOAc. The insoluble material was filtered off and washed with EtOAc. The filtrate was poured into saturated aqueous solution of NaHCO3 and extracted with EtOAc. The extract was washed with brine, dried over MgSO4 and concentrated. The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=94/6˜50/50) to give methyl 5-[3-(trifluoromethyl)phenyl]nicotinate (190.1 mg) as a pale yellow solid.

出典