Dimethylformamide → HCID 86651255, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-bromo-3-methyl-phenyl)-carbamic acid ethyl ester (210 mg) in THF (4 mL) was added n-BuLi (0.71 mL, 2.5 M solution in hexane) at −78° C. The mixture was stirred at −78° C. for 40 min, then DMF (0.31 mL) was added. The mixture was stirred at −78° C. for 40 min and then warmed up to room temperature. The reaction mixture was quenched with saturated NH4Cl aqueous solution (11 mL) and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=5:95 to 40:60) to give (4-formyl-3-methyl-phenyl)-carbamic acid ethyl ester: MS (ESI): m/z 206 (M+1); 1H NMR (CDCl3, 400 MHz) δ 10.14 (s, 1H), 7.75 (d, 1H), 7.39 (dd, 1H), 7.32 (s, 1H), 6.92 (s, 1H), 4.25 (q, 2H), 2.65 (s, 3H), 1.32 (t, 3H).

Provenance & Evidence