2-Bromopyridine → HCID 54273101, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromopyridine (1.1 ml, 11.5 mmol) and potassium carbonate (2.76 g, 20.0 mmol) were added to a solution of methyl 3-hydroxyphenylacetate (1.66 g, 9.99 mmol) in anhydrous pyridine (12 ml). The vigorously stirred reaction mixture was heated to 90° C. under a nitrogen atmosphere and then copper (II) oxide (1.99 g, 25.0 mmol) was added under a positive nitrogen flush. The reaction mixture was heated under reflux for 16 hours, allowed to cool and diluted with dichloromethane. The mixture was filtered through hyflo and concentrated in vacuo. The residue was purified by flash chromatography on silica eluting with 1:3 ethyl acetate/petrol (60°-80° ) then 1:2 ethyl acetate/petrol (60°-80° ) to give methyl [3-(2-pyridyloxy)phenyl]acetate as a pale straw-coloured oil (1.85 g, 78%); δH (360 MHz, CDCl3) 3.63 (2H, s, CH2), 3.69 (3H, s, COOCH3), 6.90 (1H, d, J 8 Hz, ArH), 6.99(1H, m, ArH), 7.06 (2H, m, ArH), 7.11 (1H, d, J 8 Hz, ArH), 7.34 (1H, t, J 8 Hz, 5'-H), 7.67 (1H, m, ArH), 8.19 (1H, m, 6"-H), m/z 243 (M+).

Provenance & Evidence