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. (2) The above 4-chloro-5-ethyl-2-thiophenecarboxaldehyde was treated in a manner similar to Reference Example 1 to give 3-bromo-1-(4-chloro-5-ethyl-2-thienylmethyl)benzene as yellow oil. APCI-Mass m/Z 347/349 (M+H+MeOH).

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-8483ace874ae46e2a1059c3605a7777d

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222219B2