反应详情

First, a synthesis method of 4-bromostilbene is described. 25.3 g (49.5 mmol) of (4-bromobenzyl)triphenylphosphoniumbromide and 5.25 g (49.5 mmol) of benzaldehyde were put into a 500 mL three-necked flask and the air in the flask was replaced with nitrogen. 250 mL of tetrahydrofuran (THF) was added to the mixture. Then, a suspension in which 6.10 g (54.4 mmol) of potassium tert-butoxide was dissolved in 60 mL of THF was dropped to this mixture. After the dropping, the reaction mixture was stirred for 24 hours at room temperature. After the reaction, the reaction mixture was washed with water and the product was extracted with ethyl acetate from the water which was used for the washing. The obtained extraction solution and the organic layer, which was washed with water, were mixed and dried with magnesium sulfate. After the drying, the mixture was suction filtrated, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solution: toluene). The obtained compound was washed with methanol and the solid was collected by suction filtration to give 3.75 g or a white powdered solid of (E)-4-bromostilbene (yield: 29.2%). A synthesis scheme (h-1) of 4-bromostilbene is shown below. Note that (Z)-4-bromostilbene was also observed in this reaction, but only (E)-4-bromostilbene was isolated and purified.

1. additionwas dropped to this mixture
2. customAfter the reaction
3. washthe reaction mixture was washed with water
4. extractionthe product was extracted with ethyl acetate from the water which
5. extractionThe obtained extraction solution
6. washthe organic layer, which was washed with water
7. additionwere mixed
8. dry with materialdried with magnesium sulfate
9. filtrationfiltrated
10. concentrationthe filtrate was concentrated
11. customThe obtained residue was purified by silica gel column chromatography (developing solution: toluene)
12. washThe obtained compound was washed with methanol
13. filtrationthe solid was collected by suction filtration
14. customto give 3.75 g