反応 #488854

反応方程式

CH2Cl2

methyl 4-bromobenzoate

4-trifluoromethylbenzylzinc chloride

→

methyl 4-(4-(trifluoromethyl)benzyl)benzoate

収率 55.0%

溶媒

THF

反応条件

後処理

1. 1
   その他the reaction tube was capped
2. 2
   温度The mixture was cooled
3. 3
   ろ過filtered through Celite
4. 4
   workup.ADDITIONWater was added to the filtrate
5. 5
   ろ過the resulting solid was filtered off
6. 6
   乾燥The organic solution was dried over MgSO4
7. 7
   濃縮concentrated
8. 8
   その他The crude product was purified by flash chromatography (silica gel, 0-10% EtOAc in heptane)

実験手順

Argon was bubbled through a mixture of methyl 4-bromobenzoate 42a (9.3 mmol, 2.0 g), 2 mL of THF, and 4-trifluoromethylbenzylzinc chloride (0.5 M in THF, 46.5 mmol, 93 mL) for 5 min. Pd(dffp)Cl2.CH2Cl2 (0.5 mol, 409 mg) was added and the reaction tube was capped and heated at 70° C. for 16 h. The mixture was cooled and filtered through Celite. Water was added to the filtrate and the resulting solid was filtered off. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by flash chromatography (silica gel, 0-10% EtOAc in heptane) to give 1.5 g (55%) of methyl 4-(4-(trifluoromethyl)benzyl)benzoate, 42b.

出典