تفاعل #821972

معادلة التفاعل

sodium bicarbonate

2-[4-(5-bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol

4-chlorophenylboric acid

4-chlorophenylboric acid

→

2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

المذيبات

1,4-dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed for 12 hours
2. 2
   درجة الحرارةthe mixture was refluxed for 8 hours
3. 3
   أخرىThe reaction mixture was evaporated down in vacuo
4. 4
   ترشيحThe precipitate was filtered off
5. 5
   غسيلwashed with diethyl ether
6. 6
   أخرىdried in vacuo

الإجراء التجريبي

40 mL of 2 N aqueous sodium bicarbonate solution was added to a suspension of 13.20 g (39.74 mmol) of 2-[4-(5-bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol, 9.32 g (59.60 mmol) of 4-chlorophenylboric acid, and 2.30 g (1.99 mmol) of tetrakis(triphenylphosphane)palladium in 400 mL of 1,4-dioxane and the mixture was refluxed for 12 hours. Another 4.66 g of 4-chlorophenylboric acid and 1.14 g of tetrakis(triphenylphosphane)palladium were added and the mixture was refluxed for 8 hours. The reaction mixture was evaporated down in vacuo and the residue was stirred with EtOAc and water. The precipitate was filtered off, washed with diethyl ether, and dried in vacuo. Yield: 10.70 g (74% of theoretical); C22H18ClNO2 (M=363.837); calc.: molpeak (M+H)+: 364/366 (Cl); found: molpeak (M+H)+: 364/366 (Cl); Rf value: 0.47 (silica gel, DCM/EtOAc 2:1).

المصدر