Benzo(B)Thiophene → 1-Benzothiophene-3-carbaldehyde

Temperature

25 °C

To a solution of benzothiophene (1.08 g, 8.0 mmol) in carbon disulfide (20 mL) at 0° C. was added titanium tetrachloride (3 mL, 27.3 mmol) followed by dichloromethyl n-butyl ether (1.24 g, 7.9 mmol) slowly dropwise. The reaction mixture was warmed to 25° C. and stirred for 1.5 h. The reaction was quenched with conc. hydrochloric acid solution (1 mL), diluted with chloroform (60 mL) and washed with water (50 mL), saturated sodium bicarbonate solution (2×30 mL) and brine (30 mL). The organic layer was dried (MgSO4), filtered, concentrated and flash chromatographed (silica gel, 2.5-5% diethyl ether in petroleum ether) to afford benzothiophene-3-carboxaldehyde (195 mg, 15% yield) as a yellow solid.

1. customThe reaction was quenched with conc. hydrochloric acid solution (1 mL)
2. additiondiluted with chloroform (60 mL)
3. washwashed with water (50 mL), saturated sodium bicarbonate solution (2×30 mL) and brine (30 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customflash chromatographed (silica gel, 2.5-5% diethyl ether in petroleum ether)

ORD record

ord-d72e388e4ff94d02ad7a6da3d3f88ea1

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515124B2