反応 #626095

反応方程式

1-bromo-3-iodobenzene

3-pyridine boronic acid

K2CO3

→

3-(3-bromophenyl)pyridine

収率 100.0%

溶媒

dioxane

反応条件

後処理

1. 1
   その他degassed with a steam of argon for 30 minutes
2. 2
   workup.STIRRINGstirred overnight
3. 3
   その他The next day, the solvent was removed by roto-evaporation
4. 4
   その他The organic layer was separated from aqueous layer
5. 5
   洗浄washed with brine (50 mL×3)
6. 6
   乾燥After drying over Na2SO4, and removal of the drying agent

実験手順

1-bromo-3-iodobenzene (1.118 g, 3.95 mol) and 3-pyridine boronic acid (0.559 g, 4.54 mol) were added to a 100 mL three neck round bottom flask. To this flask, dioxane (20 mL) and aqueous K2CO3 (2 N, 20 mL) were added. The mixture was stirred and degassed with a steam of argon for 30 minutes. Then under argon atmosphere, 50 mg (0.04 mmol) of Pd(PPh3)4 (1%) was added. The mixture was heated to 100° C. and stirred overnight. The next day, the solvent was removed by roto-evaporation and the residue was suspended into an equal amount of water (50 mL) and CH2Cl2 (50 mL). The organic layer was separated from aqueous layer and washed with brine (50 mL×3). After drying over Na2SO4, and removal of the drying agent, about 0.92 g of 3-(3-bromophenyl)pyridine product (100%) was afforded. 1H NMR (400 MHz, CDCl3) 8.85 (s, 1H), 8.65 (d, 1H), 7.87 (d, 1H), 7.75 (s, 1H), 7.57-7.52 (m, 2H), 7.41-7.35 (m, 2H).

出典