Carbon tetrabromide → Benzene, 1-(2,2-dibromoethenyl)-4-(phenylmethoxy)-

Temperature

0 °C

43 g of carbon tetrabromide was dissolved in 100 ml of dichloromethane, and then 69 g of triphenylphosphine was added to the solution while cooling in an ice bath, followed by stirring at 0° C. for ten minutes. Then, to the resulting solution, a solution of 7.0 g of 4-benzyloxybenzaldehyde dissolved in 100 ml of dichloromethane was added dropwise, followed by stirring at 0° C. for further twenty minutes. 30 ml of a saturated sodium bicarbonate aqueous solution was added slowly to the reaction solution, followed by adding 100 ml of water. The reaction solution was extracted with dichloromethane. The organic layer was washed with a saturated sodium bicarbonate aqueous solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Ether was added to the residue, and insoluble substance was removed by filtration and the filtrate was evaporated. The residue was subject to column chromatography on silica gel, and the eluate with ethyl acetate-hexane (1:20) was collected, to afford 6.4 g of the titled compound(a) as a white solid.

1. temperaturewhile cooling in an ice bath
2. additionwas added dropwise
3. stirringby stirring at 0° C. for further twenty minutes
4. extractionThe reaction solution was extracted with dichloromethane
5. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. additionEther was added to the residue, and insoluble substance
9. customwas removed by filtration
10. customthe filtrate was evaporated
11. customthe eluate with ethyl acetate-hexane (1:20) was collected
12. customto afford 6.4 g of the titled compound(a) as a white solid

ORD record

ord-b44a90cbc3f1494b92316aa605668d92

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949585B2