Trifluoromethanesulfonic anhydride → HCID 43617303, compound

Temperature

-5 °C

To a solution of N-(2-bromophenyl)acetamide (1.0 equiv.) in acetonitrile (0.4 M) at −5° C., was added trifluoromethanesulfonic anhydride (2.0 equiv.) dropwise and the mixture was stirred for 5 min. Trimethylsilyl azide (4.0 equiv.) was added slowly while maintaining the temperature at −5° C., then the mixture was stirred at 0° C. for 80 mins. The mixture was poured into ice-cold sodium bicarbonate solution, extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude residue. The residue was purified by silica gel column chromatography (16% ethyl acetate in petroleum ether) to give the desired product (44% yield) as a yellow solid. MS (ESI) m/z 239.1 [M+H]+.

1. stirringthe mixture was stirred at 0° C. for 80 mins
2. additionThe mixture was poured into ice-cold sodium bicarbonate solution
3. extractionextracted with ethyl acetate
4. washthe combined organic layers were washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto afford the crude residue
9. customThe residue was purified by silica gel column chromatography (16% ethyl acetate in petroleum ether)

ORD record

ord-3cce7dda36814480b66629589ced010b

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156798B2