Chlorosuccinimide → HCID 66922119, compound

Temperature

125 °C

To a stirred solution of 9.64 g (43 mmol) of the compound of step 1 in DCM (250 ml) was added N-chlorosuccinimide (6.02 g, 45 mmol) in one portion at room temperature. The reaction mixture was stirred for 12 h and the solvent was evaporated. The remaining residue was dissolved in a mixture of acetic acid (180 ml) and phosphoric acid (31 ml) and heated to 125° C. for 1 h. The solution was cooled to room temperature and concentrated in vacuo. The remaining residue was poured onto ice and the aqueous phase was extracted with EA. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The remaining oil was purified by column chromatography on silica gel (EA/HEP) to give 4.80 g of the title compound.

1. customthe solvent was evaporated
2. dissolutionThe remaining residue was dissolved in a mixture of acetic acid (180 ml) and phosphoric acid (31 ml)
3. temperatureThe solution was cooled to room temperature
4. concentrationconcentrated in vacuo
5. additionThe remaining residue was poured onto ice
6. extractionthe aqueous phase was extracted with EA
7. washThe combined organic phases were washed with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customthe solvent was removed under reduced pressure
11. customThe remaining oil was purified by column chromatography on silica gel (EA/HEP)

ORD record

ord-8bb35755212c408ca60a0d820507a02f

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580813B2