Dimethylformamide → 5-Chloro-1-benzothiophene-2-carbaldehyde

Participants

Reaction Steps

To a solution of 5-chlorobenzo[b]thiophene (6.14 g) in THF (120 ml) was added n-BuLi (1.6 M solution in hexane, 27.3 ml) at −78° C., and the mixture was stirred for 2 hours. To this mixture was added DMF (8.5 ml), and the mixture was stirred for 1 hour at −78° C. to −30° C. The reaction was quenched by the addition of water and allowed to warm to room temperature. The organic layer was separated, diluted with ethyl acetate, washed with 10% citric acid solution, brine, dried over MgSO4, and concentrated. The residue was titurated with diisopropylether to give the titled compound as colorless crystals (5.92 g).

Provenance & Evidence