Dimethylformamide → m-Ethylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3-ethylbenzene (5 g, 27.2 mmol) in THF (135 mL) at −78° C. was added butyl lithium (1.6 M in hexanes, 18 mL, 28.8 mmol) dropwise. The mixture was stirred at −78° C. for 5 min. DMF (2.1 mL, 27.2 mmol) was added and the mixture was warmed to ambient temperature over 2 h. The mixture was diluted with diethyl ether (500 mL), washed with sat. NaHCO3 and brine, dried (Na2SO4) and concentrated to yield 4 g of Intermediate 370.1 as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (t, J=7.58 Hz, 3H) 2.73 (q, J=7.58 Hz, 2H) 7.39-7.51 (m, 2H) 7.64-7.76 (m, 2H) 9.99 (s, 1H).

Provenance & Evidence