Sodium hydride → HCID 58335249, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% in mineral oil, 72 mg, 1.8 mmol) in DMF (3.30 mL) at 0° C. was added dropwise a mixture of 2-bromo-6-(bromomethyl)pyridine (493 mg, 1.97 mmol) and methyl glycolate (148 mg, 1.64 mmol) in DMF (1.5 mL), and the reaction mixture was stirred for 2 hours at 0° C. The reaction mixture was quenched with 1:1 isopropanol:methanol (5 mL) and then poured over ice. The reaction mixture was diluted with water and diethyl ether. The organics were separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford methyl [(6-bromopyridin-2-yl)methoxy]acetate. MS ESI calc'd. for C9H11BrNO3 [M+H]+ 260 and 262. found 260 and 262. 1H NMR (500 MHz, CDCl3) δ 7.58 (t, J=7.7 Hz, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 4.72 (s, 2H), 4.23 (s, 2H), 3.78 (s, 3H).

Provenance & Evidence