5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE

To a stirred solution of 5-bromo-2-chloro-4-iodopyridine (20.0 g, 63.09 mmol, 1.0 eq) in DMF (200 mL), methyl 2, 2-difluoro-2-(fluorosulfonyl)acetate (16.15 mL, 126.18 mmol, 2.0 eq) and Cul (24.02 g, 126.18 mmol, 2.0 eq) were added at RT under argon atmosphere and the reaction mixture was heated to 100°C for 6h. TLC analysis indicated a non-polar spot. The reaction mixture was diluted with water (200 mL) and filtered off and washed with w-pentane (1L) and cold water (3L). The separated organic layer was dried over sodium sulfate and concentrated under reduced pressure at 30°C. The crude compound was purified by column chromatography (Silica gel, 100-200 mesh) using 5percent EtOAc in pet ether as an eluent to afford the title compound (9.0 g, 55.2percent) as a liquid compound. TLC: 5percent EtOAc in pet ether; RTo a stirred solution of 5-bromo-2-chloro-4-iodopyridine (20.0 g, 63.09 mmol) in DMF (200 mL), methyl 2, 2-difluoro-2-(fluorosulfonyl)acetate (16.15 mL, 126.18 mmol) and Cul (24.02 g, 126.18 mmol) were added at RT under argon atmosphere. The reaction mixture was heated to 100 °C for 6 hours. The reaction mixture was diluted with water (200 mL) filtered off and washed with w-pentane (2 X 500 mL) and cold water (3 X 1000 mL). The separated organic layer dried over with sodium sulfate and concentrated under reduced pressure at 30 °C to give the crude compound. That was purified by column chromatography (5percent pet ether: EtO Ac) that resulted in the title compound (9.0g, 44percent) as a liquid compound. TLC: 5percent EtO Ac in pet ether. LCMS [M+H]

Molecular Weight:260.44
XLogP3:3.4
Hydrogen Bond Acceptor Count:4
Exact Mass:258.90112
Monoisotopic Mass:258.90112
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes