1-(5-Bromo-2-fluoropyridin-3-yl)ethanone

A solution of pyridinium dichromate (55.4 g, 147 mmol) in DCM (100 mL) was brought to 0° C. and a solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanol (10.8 g, 49.1 mmol) in DCM (30 mL) was added. The reaction was allowed to warmed to room temperature and stirred for 48 h. The mixture was filtered through Celite, washed with DCM and concentrated to afford 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (11 g, 51 mmol, 100percent yield) as a light yellow solid. LC/MS (ESIl -(5 jrorao~2~flero-3-pyrtdyl)tHiiaoe: To a solution of the above compound (3.15 g, 14.32 mmol, L0 eq.) in DCM (95.5 mStep 3:76 77To a mixture of PDC (365 g, 0.97 mol) and CHPreparative Example 7 Step 1: l-(5-bromo-2-fluoropyridin-3-yl)ethanone To a solution of diisopropylamine (46.3 g, 458.4 mmol) in tetrahydrofuran (lOOOmL) was added butyllithium (176 mL, 440 mmol, 2.5 M) at -78 °C under nitrogen. After addition, the reaction mixture was stirred for 30 min at -78 °C. 5-bromo-2-fluoropyridine (86.7 g, 442.3 mmol) was added (keeping the temperature under -65 °C). After addition, the mixture was stirred for 1 h. N-methoxy- N-methylacetamide (50 g, 485.4 mmol) was added and stirred at -78 °C for 1 h. The reaction mixture was quenched with water (lOOOmL), extracted with ethyl acetate (3 x 500 mL), washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 0.5percent ethyl acetate in petroleum ether) affording 1- (5-bromo-2-fluoropyridin-3-yl)ethanone (43 g, 44.6 percent): H NMR (400 MHz, Chloroform-d): δ 8.46- 8.42 (m, 2H), 2.70 (s, 3H).

Molecular Weight:218.02
XLogP3:1.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:216.95385
Monoisotopic Mass:216.95385
Topological Polar Surface Area:30
Heavy Atom Count:11
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes