반응 #512421

반응 방정식

1,3-dibromobenzene

5-methyl-2-tri-n-butylstannylpyridine

lithium chloride

→

title product

1,3-di(5-methyl-2-pyridyl)benzene

용매

toluene

반응 조건

후처리

1. 1
   기타was degassed
2. 2
   기타by bubbling argon through the mixture for 15 minutes
3. 3
   온도The reaction mixture was heated
4. 4
   온도under reflux for 24 h
5. 5
   여과was filtered through small pad of silica gel, which
6. 6
   세척was then washed with ethyl acetate
7. 7
   기타The filtrate was evaporated to dryness
8. 8
   기타the product was purified by column chromatography (silica gel, hexane/ethyl acetate, 1/1)

실험 절차

A mixture of 1,3-dibromobenzene (1.88 g, 8 mmol), 5-methyl-2-tri-n-butylstannylpyridine (7.18 g, 18.8 mmol), lithium chloride (28 g, 0.67 mol), bis(triphenylphosphine)palladium dichloride (360 mg, 0.5 mmol) and toluene (150 cm3) was degassed by bubbling argon through the mixture for 15 minutes. The reaction mixture was heated under reflux for 24 h. The mixture was then allowed to cool to room temperature and was filtered through small pad of silica gel, which was then washed with ethyl acetate. The filtrate was evaporated to dryness and the product was purified by column chromatography (silica gel, hexane/ethyl acetate, 1/1) to give the title product as a colourless solid. Yield 728 mg, 35%. δH (270 MHz; CDCl3): 2.36 (6H, s, 2×CH3), 7.54 (1H, t, J 8.0, 5-H), 7.56 (2H, dd, J 8.2 and 2.1, 2×py 4-H), 7.72 (2H, d, J 8.2, 2×py 3-H), 7.99 (2H, dd, J 8.0 and 1.8, 4-H, 6-H), 8.52 (2H, d, J 2.1, 2×py 6-H), 8.54 (1H, t, J 1.8, 2-H).

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