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

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).

1. stirringthe mixture was stirred for 1 hour at −78° C. to −30° C
2. customThe reaction was quenched by the addition of water
3. customThe organic layer was separated
4. additiondiluted with ethyl acetate
5. washwashed with 10% citric acid solution, brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-b01a1e96291240ea976d8379906ed0ad

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06420375B1