Water → 4-Chloro-5-ethyl-2-thiophenecarboxaldehyde

To a solution of 5-ethyl-2-thiophenecarboxaldehyde (6.0 g) in N,N-dimethylformamide (60 ml) was added N-chlorosuccinimide (8.57 g), and the mixture was stirred at room temperature for 2 hours, and subsequently stirred under heating at 60° C. for 2 hours. N-chlorosuccinimide (4.00 g) was further added thereto, and the mixture was further stirred under heating at 60° C. for 2 hours. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate, washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=33:1) to give 4-chloro-5-ethyl-2-thiophenecarboxaldehyde (3.1 g) as colorless oil.

1. stirringsubsequently stirred
2. temperatureunder heating at 60° C. for 2 hours
3. stirringthe mixture was further stirred
4. temperatureunder heating at 60° C. for 2 hours
5. extractionthe mixture was extracted with ethyl acetate
6. washwashed with brine
7. dry with materialdried over sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=33:1)

ORD record

ord-aec66b8abc954a41a09a3b2a5d459365

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2