Ethyl Acetate → HCID 86634715, compound

Participants

Reaction Steps

Methyl 3-hydroxybenzoate (2.88 g, 18.9 mmol) was added to a mixture of 60% sodium hydride in mineral oil (0.757 g, 18.9 mmol) in DMF (20 mL). The reaction mixture was stirred for 20 minutes and then cooled in an ice bath. 2-Chloro-4-nitropyridine (3.00 g, 18.9 mmol) was added and the reaction mixture was stirred for 1 hour at 0° C., and then overnight at room temperature. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed twice with water and brine, dried, and concentrated. The residue was purified by MPLC (Biotage) eluting with 5:1 hexane:ethyl acetate to afford methyl 3-(2-chloropyridin-4-yloxy)benzoate (4.49 g, 90.0% yield) as a thick oil. 1H NMR (CDCl3) δ 8.26 (d, 1H), 7.98 (d, 1H), 7.77 (s, 1H), 7.54 (t, 1H), 7-31 (d, 1H), 6.82 (s, 1H), 6.79 (d, 1H).

Provenance & Evidence