反応 #1583825

反応方程式

methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate

product

methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate

[3-(trifluoromethoxy)phenyl]boronic acid

cesium carbonate

triphenylphosphine

→

title compound

methyl 2-[4-chloro-3′-(trifluoromethoxy)[1,1′-biphenyl]-3-yl]hydrazine carboxylate

溶媒

diethyl ether

toluene

methanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at refluxed for 24 h
3. 3
   温度After cooling
4. 4
   洗浄washed with water
5. 5
   乾燥After drying over sodium sulfate
6. 6
   その他the solvent was removed under reduced pressure
7. 7
   その他The residue was purified by flash chromatography
8. 8
   その他to afford a solid matieral (1.3 g), which
9. 9
   workup.ADDITIONa mixture of starting material

実験手順

A mixture of methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate (i.e. the product of Step B) (1.27 g, 4.5 mmol), [3-(trifluoromethoxy)phenyl]boronic acid (1.85 g, 9 mmol), cesium carbonate (2.9 g, 9 mmol), tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) and triphenylphosphine (1.2 g, 4.5 mmol) in toluene (60 mL) and methanol (60 mL) was heated at refluxed for 24 h. After cooling, the reaction mixture was taken up in diethyl ether and washed with water. After drying over sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by flash chromatography using 25% ethyl acetate in hexanes as eluant to afford a solid matieral (1.3 g), which was a mixture of starting material and the title compound.

出典