Dimethylformamide → 2-Fluoro-5-(2-methyl-1,3-dioxolan-2-yl)benzaldehyde

Participants

Reaction Steps

Intermediate 416.1 (1 g, 3.83 mmol) in THF (20 mL) was cooled to −78° C. before adding 1.6 M n-BuLi (2.63 mL, 4.2 mmol) drop-wise. The reaction was stirred for 10 min before quenching with DMF (0.6 mL, 7.7 mmol) and allowing to warm to rt. The crude reaction mixture was quenched with NH4Cl (10 mL), extracted with EtOAc (3×10 mL), washed organic layer with H2O, brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 550 mg of Intermediate 416.2. 1H NMR (400 MHz, CDCl3) δ ppm 1.63 (s, 3H) 3.51-3.92 (m, 2H) 3.90-4.35 (m, 2H) 7.09-7.19 (m, 1H) 7.65-7.79 (m, 1H) 7.99 (dd, J=6.81, 2.42 Hz, 1H) 10.35 (s, 1H).

Provenance & Evidence