Synthesis
GENERAL STEPS: To a screw-capped tube, 4-formylphenylboronic acid (450 mg, 3 mmol), ethyl bromoacetate (0.22 mL, 2 mmol), potassium carbonate (830 mg, 6 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 46 mg, 0.05 mmol), tris(1-naphthyl)phosphine (62 mg, 0.15 mmol), water (0.5 mL) and tetrahydrofuran (THF, 4.5 mL). The reaction mixture was degassed with nitrogen for 5 min and then the reaction was stirred at 65 °C in an oil bath for 18 h. The reaction was carried out in the presence of a nitrogen gas. After completion of the reaction, it was cooled to room temperature, diluted with ethyl acetate (50 mL) and washed with water (2 x 50 mL). The organic phase was filtered through a phase separator and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography eluting with a gradient of 0-20% ethyl acetate/isohexane solution to afford the target product ethyl 2-(4-formylphenyl) acetate as a colorless oil (327 mg, 57% yield).1H NMR (400 MHz, CDCl3) δ: 9.99 (s, 1H), 7.83 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 8.0 Hz, 2H), 4.19-4.12 (m, 2H), 3.70 (s, 2H), 1.28-1.20 (m, 3H).LCMS (Method 1): [MH+] = 193, retention time 3.58 min.
References
[1] Tetrahedron, 2010, vol. 66, # 42, p. 8238 - 8241
[2] Chemical Communications, 2001, # 7, p. 669 - 670
[3] Patent: WO2014/86852, 2014, A1. Location in patent: Page/Page column 67; 68
[4] Patent: US2014/155427, 2014, A1. Location in patent: Page/Page column
