Dimethylformamide → 4-Formyl-3-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-3-methylbenzonitrile (20 g, 102 mmol) in THF (500 mL) at −100° C. was slowly added a solution of n-Buli 1.6M in hexanes (70 mL, 112 mmol). DMF (11 mL, 143 mmol) was then added and the mixture was allowed to warm to −50° C. over 30 min. The reaction mixture was quenched with brine. The reaction mixture was diluted with EtOAc and extracted with brine. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 80:20) the residue was triturated in Et2O/hexane 90:10 to afford the title compound. tR: 0.86 min (LC-MS 2); Rf=0.40 (hexane/EtOAc, 8:2).

Provenance & Evidence