Carbon tetrabromide → 1-(Benzyloxy)-3-(2,2-dibromoethenyl)benzene

To a solution of triphenylphosphine (119.6 g) in methylene chloride (420 mL) at 0° C. was added a solution of carbon tetrabromide (75.72 g) in methylene chloride (90 mL). After completion of the addition, the mixture was stirred for 10 min. Then a solution of 3-(benzyloxy)benzaldehyde (J.A.C.S., 99, 2571 (1977)) (40 g) in methylene chloride (150 ml) was added. The mixture was stirred for 16 hrs at -5° C. After warming to room temperature, the organic layer was washed with saturated sodium bicarbonate (2×150 ml) and brine (1×150 ml), then dried over magnesium sulfate, filtered and the mixture was concentrated. Ether (300 ml) was added, causing the formation of a precipitate which was filtered. The filtrate was concentrated and the process repeated 2 times. Finally, the filtrate was concentrated and chromatographed using 10% ethyl acetate in hexane, affording the title compound as a solid.

1. additionAfter completion of the addition
2. stirringThe mixture was stirred for 16 hrs at -5° C
3. washthe organic layer was washed with saturated sodium bicarbonate (2×150 ml) and brine (1×150 ml)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationthe mixture was concentrated
7. additionEther (300 ml) was added
8. filtrationwas filtered
9. concentrationThe filtrate was concentrated
10. concentrationFinally, the filtrate was concentrated
11. customchromatographed

ORD record

ord-f340f3b792384e2dabb4ebfa6eedc536

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05227399