Dimethylformamide → 2,6-Dichloro-4-(ethylthio)benzaldehyde

A solution of 3,5-dichlorophenyl ethyl sulfide (1.0 g, 4.8 mmol) in tetrahydrofuran (4 mL) was cooled to −78° C. A solution of n-butyllithium (4.5 mL, 1.6 M in hexane) was added dropwise and the mixture was stirred at −78° C. for 45 minutes. N,N-dimethylformamide (4.47 mL, 57.7 mmol) was added and the mixture was stirred at −78° C. for 1 hour. The mixture was stirred at room temperature for 2 hours. The mixture was quenched with ice water and extracted three times with ethyl acetate. The combined extracts were dried with sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel to give the desired product (1.1 g, 97%). 1H NMR (CDCl3) δ 10.40 (s, 1H), 7.20 (s, 2H), 3.00 (m, 2H), 1.4 (m, 3H). LC/MS: 235 (M+H)+.

1. stirringthe mixture was stirred at −78° C. for 1 hour
2. stirringThe mixture was stirred at room temperature for 2 hours
3. customThe mixture was quenched with ice water
4. extractionextracted three times with ethyl acetate
5. dry with materialThe combined extracts were dried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by chromatography on silica gel

ORD record

ord-3b93899ba83d4b91b0ba8ae530658e34

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563541B2