تفاعل #1129005

معادلة التفاعل

2,6-dibromopyridine

phenylboronic acid

potassium carbonate

→

product

المردود 34.4%

2-bromo-6-phenylpyridine

المردود 34.4%

المذيبات

dimethoxyethane

water

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a 3-neck 1 L round-bottom flask fitted with a condenser, nitrogen inlet
2. 2
   أخرىNitrogen was bubbled directly into the mixture for 15 minutes
3. 3
   workup.ADDITIONTetrakis(triphenylphosphine)palladium (0) was added (1.85 g, 1.60 mmol)
4. 4
   درجة الحرارةthe reaction mixture was heated to reflux
5. 5
   درجة الحرارةof heating
6. 6
   workup.ADDITIONdiluted with water and ethyl acetate
7. 7
   أخرىThe layers were separated
8. 8
   استخلاصthe aqueous layer extracted with ethyl acetate
9. 9
   تجفيفThe organic layers were dried over magnesium sulfate
10. 10
    ترشيحfiltered
11. 11
    أخرىevaporated
12. 12
    أخرىThe material was purified by column chromatography
13. 13
    غسيلeluting with 2% ethyl acetate/hexanes
14. 14
    workup.DISTILLATIONfollowed by vacuum distillation
15. 15
    أخرىat 150° C

الإجراء التجريبي

In a 3-neck 1 L round-bottom flask fitted with a condenser, nitrogen inlet, and 2 stoppers was added 2,6-dibromopyridine (15.3 g, 64.58 mmol), phenylboronic acid (7.87 g, 64.58 mmol), and potassium carbonate (17:85 g, 129.16 mmol) in 228 mL of dimethoxyethane and 150 mL of water. Nitrogen was bubbled directly into the mixture for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) was added (1.85 g, 1.60 mmol) and the reaction mixture was heated to reflux. The reaction was complete after 3 h of heating. It was cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous layer extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered, and evaporated. The material was purified by column chromatography eluting with 2% ethyl acetate/hexanes followed by vacuum distillation using a Kugelrohr collecting product at 150° C. 5.2 g of product was obtained (34%)

المصدر