Tetra-n-butylammonium tribromide → Tert-butyl (1-(4-(2-bromoacetyl)phenyl)cyclobutyl)carbamate

Temperature

40 °C

To a solution of tert-butyl (1-(4-acetylphenyl)cyclobutyl)carbamate (0.1 g, 1 eq.) in chloroform (3.5 mL) and methanol (1.5 mL) was added the tetrabutyl ammonium tribromide (0.175 g, 1.05 eq.). The mixture was stirred at 40° C. for 90 minutes. The reaction mixture was diluted with dichloromethane (10 mL), washed with water (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The product was purified by column chromatography (10% ethyl acetate in dichloromethane), giving tert-butyl (1-(4-(2-bromoacetyl)phenyl)cyclobutyl)carbamate (0.1 g, 78%) as a colorless oil. LCMS: 312 [M−tBu+H], 314 [M−tBu+H].

1. washwashed with water (10 mL)
2. dry with materialdried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe product was purified by column chromatography (10% ethyl acetate in dichloromethane)

ORD record

ord-8a0441fe7a0e46158b6fdf4866d02349

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569331B2