Ethyl trifluoroacetate → 1-(5-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-one

Temperature

-78 °C

2,5-Dibromopyridine (7.11 g, 30 mmol) was dissolved in dry toluene (200 mL) and cooled to −78° C. n-BuLi (14.4 mL, 2.5 M in THF, 36 mmol) was added dropwise. The mixture was stirred at −78° C. for 2 hours and ethyl trifluoroacetate (6.39 g, 45 mmol) was added. The resulting mixture was allowed to warm to room temperature slowly and stirred at room temperature for 30 min. The reaction was quenched with NH4Cl (aq.) and extracted with EtOAc. The organics were dried and concentrated and the resulting residue was purified by column chromatography (silica gel, 0-30% EtOAc/Hexane) to give the product 1-(5-bromopyridin-2-yl)-2,2,2-trifluoroethanone (5.87 g).

1. additionwas added dropwise
2. temperatureto warm to room temperature slowly
3. stirringstirred at room temperature for 30 min
4. customThe reaction was quenched with NH4Cl (aq.)
5. extractionextracted with EtOAc
6. customThe organics were dried
7. concentrationconcentrated
8. customthe resulting residue was purified by column chromatography (silica gel, 0-30% EtOAc/Hexane)

ORD record

ord-5c306c56ab8a48539a268a1480bd2e0f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227971B2