Triacetoxyperiodinane → 1-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one

1-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethanol (2 g, 7.66 mmol) was dissolved in dry CH2Cl2 (20 mL) and argon gas was purged for 10 min. Dess-Martin periodinane (3.56 g, 8.4 mmol) was added to the reaction mixture at 0° C. The reaction mixture was allowed to warm up to room temperature and further stirred for 3 h. The reaction mixture was then quenched with saturated NaHCO3 solution and the organic product was extracted with EtOAc. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether) to afford 1-(5-bromothiophen-2-yl)-2,2,2-trifluoroethanone (0.8 g, yield 42%). 1H NMR (400 MHz, CDCl3) δ 7.72-7.71 (m, 1H), 7.24-7.23 (d, J=4.3 Hz, 1H).

1. customargon gas was purged for 10 min
2. customThe reaction mixture was then quenched with saturated NaHCO3 solution
3. extractionthe organic product was extracted with EtOAc
4. customSolvent was removed under reduced pressure
5. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether)

ORD record

ord-ac1681d8e4664371a8b1dda234b61f58

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08981084B2