تفاعل #158256

معادلة التفاعل

m-methoxy-phenylboronic acid

2,6-dichloropyridine

potassium carbonate

triphenylphosphine

→

2-chloro-6-(3-methoxyphenyl)pyridine

المذيبات

water

dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   أخرىwas prepared
2. 2
   أخرىNitrogen was bubbled directly in the mixture for 20 minutes
3. 3
   workup.ADDITIONThen palladium acetate was added (0.44 g, 2.0 mmol)
4. 4
   أخرىNitrogen was bubbled again in the mixture for another 10 minutes
5. 5
   درجة الحرارةThe mixture was heated
6. 6
   درجة الحرارةto reflux under nitrogen overnight
7. 7
   أخرىThe organic layer was separated
8. 8
   استخلاصthe aqueous layer was extracted with dichloromethane
9. 9
   تجفيفThe combined organic layers were dried over magnesium sulfate
10. 10
    ترشيحfiltered
11. 11
    أخرىevaporated
12. 12
    أخرىThe mixture was purified by silica column with up to 10% ethyl acetate in hexanes

الإجراء التجريبي

A mixture of m-methoxy-phenylboronic acid (10 g, 65.8 mmol), 2,6-dichloropyridine (9.7 g, 65.8 mmol), potassium carbonate (27.3 g, 197.4 mmol), triphenylphosphine (2.07 g, 7.9 mmol), dimethoxyethane 250 mL and water 80 mL was prepared. Nitrogen was bubbled directly in the mixture for 20 minutes. Then palladium acetate was added (0.44 g, 2.0 mmol). Nitrogen was bubbled again in the mixture for another 10 minutes. The mixture was heated to reflux under nitrogen overnight. The reaction mixture was cooled to room temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The mixture was purified by silica column with up to 10% ethyl acetate in hexanes to gain 6.5 g colorless oil (45%).

المصدر