反応 #61756

反応方程式

sodium carbonate

4-trifluoromethyl-phenylboronic acid

5-bromo-pyridine-2-carbaldehyde

→

5-(4-trifluoromethyl-phenyl)-pyridine-2-carbaldehyde

収率 66.7%

溶媒

1,2-dimethoxyethane

反応条件

後処理

1. 1
   温度the mixture heated
2. 2
   その他for 18 hours
3. 3
   ろ過filtered
4. 4
   その他the filtrate evaporated
5. 5
   洗浄washed twice with water
6. 6
   乾燥dried over sodium sulphate
7. 7
   その他evaporated

実験手順

439 mg (0.38 mmol) Pd(PPh3)4 was added under argon at room temperature (r.t.) to a solution of 823 mg (3.76 mmol) 5-bromo-pyridine-2-carbaldehyde in 30 ml 1,2-dimethoxyethane and stirred for 15 min. 14.5 ml (29.0 mmol) of 2 M sodium carbonate solution and 1.00 g (5.27 mmol) 4-trifluoromethyl-phenylboronic acid were added and the mixture heated to boiling temperature for 18 hours (h). The reaction mixture was cooled to room temperature (r.t.), filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 630 mg (48%) of 5-(4-trifluoromethyl-phenyl)-pyridine-2-carbaldehyde.

出典