تفاعل #78090

معادلة التفاعل

3-nitrophenylboronic acid

3-bromopyridine

potassium carbonate

1,3-propanediol

→

3-(3-nitrophenyl)pyridine

المردود 84.3%

المذيبات

dimethoxyethane

water

dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   أخرىwas removed under reduced pressure
2. 2
   workup.STIRRINGthe residue was stirred with additionally 200 ml water overnight
3. 3
   ترشيحThe precipitate was filtered off
4. 4
   استخلاصextracted with aqueous hydrochloric acid (4M, 300 ml)
5. 5
   workup.ADDITIONby addition of aqueous sodium hydroxide (12M)
6. 6
   ترشيحThe product was filtered off
7. 7
   غسيلwashed with water
8. 8
   أخرىdried with suction

الإجراء التجريبي

A mixture of 3-nitrophenylboronic acid (50 g, 0.3 mol), 3-bromopyridine (48 ml, 0.5 mol), potassium carbonate (207 g, 1.5 mol), 1,3-propanediol (107 ml, 1.5 mol) and tetrakis(triphenylphosphine)palladium(0) (0.5 g) in a mixture of water (200 ml) and dimethoxyethane (400 ml) was stirred in a nitrogen atmosphere at 80° C. for 3 hours. After cooling the dimethoxyethane was removed under reduced pressure and the residue was stirred with additionally 200 ml water overnight. The precipitate was filtered off and extracted with aqueous hydrochloric acid (4M, 300 ml). The extract was rendered alkaline by addition of aqueous sodium hydroxide (12M). The product was filtered off, washed with water and dried with suction to yield 3-(3-nitrophenyl)pyridine (50.6 g, 84%).

المصدر