Carbon tetrabromide → HCID 86657052, compound

Temperature

-15 °C

Into a 10 L 3-necked roundbottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of triphenylphosphine (516.6 g, 1.970 mol) in dichloromethane (2,000 ml). The solution was cooled to −15° C. and a solution of carbontetrabromide (327.3 g, 985.8 mmol) in dichloromethane (1,000 ml) was added over a period of 120 minutes. Then a solution of tert-butyl 2-(2-oxoethyl)pyrrolidine-1-carboxylate (105 g, 493 mmol) in dichloromethane (1,000 ml) was added dropwise over a period of 120 minutes. The resulting solution was allowed warm to warm to 0° C., and stir for 20 minutes. The resulting solution was diluted with 4,000 ml of petroleum ether. The mixture was filtered and concentrated. The residue was purified by flash column chromatography (ethylacetate/petroleum ether gradient) to afford tert-butyl 2-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate.

1. customInto a 10 L 3-necked roundbottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. temperatureThe resulting solution was allowed warm
4. temperatureto warm to 0° C.
5. filtrationThe mixture was filtered
6. concentrationconcentrated
7. customThe residue was purified by flash column chromatography (ethylacetate/petroleum ether gradient)

ORD record

ord-46fb7072a30044cea10ce3159127ab1d

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2