Dimethylformamide → 3-Bromo-5-ethyl-2-fluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.449 mL, 3.20 mmol) in 10 mL THF at −15° C., was added BuLi (1.6M, 1.85 mL, 2.95 mmol). The mixture was stirred 10 min at −10° C., then was cooled to −78° C. A solution of 2-bromo-4-ethyl-1-fluorobenzene (228.1) in 2 mL THF was added, then the mixture was stirred at −70° C. for 25 min. DMF (0.381 mL, 4.92 mmol) was added, then the reaction was removed from the cooling bath and stirred 30 min. The reaction was quenched with sat. NH4Cl, then was diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0-20% EtOAc/hexanes gradient) to afford 429 mg of Intermediate 398.1 at a colorless solid. LCMS (2 min gradient) RT=1.70 min, 231.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (t, J=7.69 Hz, 3H) 2.67 (q, J=7.47 Hz, 2H) 7.61-7.66 (m, 2H) 10.33 (s, 1H).

Provenance & Evidence