Reaktion #675996

Reaktionsgleichung

4-chloro-5-iodo-2-methoxybenzenamine

2,5-dichlorophenylboronic acid

Na2CO3

→

desired product

Ausbeute 75.8%

2′,5′,6-Trichloro-4-methoxy-[1,1′-biphenyl]-3-amine

Ausbeute 75.8%

Lösungsmittel

1,4-dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1)

Vorschrift

A mixture of 4-chloro-5-iodo-2-methoxybenzenamine (4.1 g, 14.5 mmol), 2,5-dichlorophenylboronic acid (3.3 g, 17.4 mmol), Pd(PPh3)4 (500 mg, 1.45 mmol) and Na2CO3 (4.7 g, 43.5 mmol) in 1,4-dioxane (150 mL) and water (15 mL) was stirred at 80° C. under argon for 16 h. The mixture was allowed to cool to room temperature, and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to afford the desired product (3.3 g, 75.8% yield) as an off-white solid.

Quelle