1-(6-BROMOPYRIDIN-2-YL)-2,2,2-TRIFLUOROETHANONE synthesis
- Product Name:1-(6-BROMOPYRIDIN-2-YL)-2,2,2-TRIFLUOROETHANONE
- CAS Number:886364-57-4
- Molecular formula:C7H3BrF3NO
- Molecular Weight:254
626-05-1
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Yield:886364-57-4 64.81%
Reaction Conditions:
Stage #1: 2,6-Dibromopyridinewith n-butyllithium in tetrahydrofuran;hexane at -78; for 1 h;Inert atmosphere;
Stage #2: 2,2,2-Trifluoro-1-morpholin-4-yl-ethanone in tetrahydrofuran;hexane at -78;Inert atmosphere;
Steps:
1 Step-1: Synthesis of 1-(6-bromopyridin-2-yl)-2,2,2-trifluoroethanone
To a stirred solution of 2,6-dibromopyridine (5.0 g, 2.12 mmol) in THF (50 mL) at -78°C was added n-Butyl lithium (2.5M in hexane) (12.5 mL, 3.18 mmol) under nitrogen and stirred for 1h at same temperature. 2,2,2-trifluoro-1-morpholinoethanone (5.06 g, 2.76 mmol) was then added drop wise to the reaction mixture, stirred for 1h at -78°C. Progress of reaction was monitored by TLC. After reaction completion reaction mass was quenched with ice cold water. Phases separated and aqueous layer was extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Crude was purified by silica gel (100-200 mesh) column chromatography using 18% ethyl acetate in hexane as eluent to obtain 1-(6-bromopyridin-2-yl)-2,2,2-trifluoroethanone (3.5 g, 64.81%) as a colourless oil,
References:
WO2020/240586,2020,A1 Location in patent:Page/Page column 155
