反应详情

温度

130 °C

A mixture of 3,5-dibromobenzaldehyde (8.21 g, 31.1 mmoles), 3,5-bis(3′,5′-di-t-butylstyryl)styrene (41.4 g, 77.7 mmoles), anhydrous sodium carbonate (6.59 g, 62.2 mmoles), trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) (58.3 mg, 0.062 mmoles, 0.1 mole %), 2,6-di-t-butylcresol (1.71 g, 7.77 mmoles) and anhydrous N,N-dimethylacetamide (100 mL) was degassed extremely thoroughly whilst stirring under oil-pump vacuum, purging with argon. The reaction mixture was then heated under argon at 130° C. for 17 hours. After further addition of anhydrous N,N-dimethylacetamide (100 mL), the reaction mixture was degassed for a second time and then heated at 130° C. for a further 5.5 hours. Further anhydrous N,N-dimethylacetamide (100 mL) was then added and the reaction was continued for a further 1 hour. The resulting sludge was washed with distilled water (3×250 mL) and dissolved in dichloromethane (1500 mL). The organic fraction was washed with distilled water (500 mL), dried over anhydrous sodium sulphate and evaporated to give a cream solid. The crude product was recrystallized from dichloromethane/pet. ether (60-80) three times before chromatography on flash silica using chloroform-pet.ether (60-80) (2:3) as the eluent gave a white solid of 3,5-bis[3′,5′-bis(3″,5-″-di-t-butylstyryl)styryl]benzaldehyde (25.2 g, 69%); δH(500 MHz; CDCl1) 1.41 (72H, s, t-Bu), 7.20 and 7.32 (8H, d, J 16, G-2 vinyl H), 7.34 and 7.38 (4H, d, J 16.5, G-1 vinyl H), 7.42 (4H, dd, J 2, sp H), 7.46 (8H, d, J 2, sp H), 7.67 (4H, s, G-1 bp H), 7.69 (2H, s, G-1 bp H), 8.00 (3H, s, cp H) and 10.14 (1H, s, CHO) which is identical to that reported.

1. customwas degassed extremely thoroughly
2. custompurging with argon
3. additionAfter further addition of anhydrous N,N-dimethylacetamide (100 mL)
4. customthe reaction mixture was degassed for a second time
5. temperatureheated at 130° C. for a further 5.5 hours
6. additionFurther anhydrous N,N-dimethylacetamide (100 mL) was then added
7. washThe resulting sludge was washed with distilled water (3×250 mL)
8. dissolutiondissolved in dichloromethane (1500 mL)
9. washThe organic fraction was washed with distilled water (500 mL)
10. dry with materialdried over anhydrous sodium sulphate
11. customevaporated
12. customto give a cream solid
13. customThe crude product was recrystallized from dichloromethane/pet. ether (60-80) three times before chromatography on flash silica