Dimethylformamide → 5-Cyano-2-fluorobenzaldehyde

Diisopropylamine (2.80 ml, 19.8 mmol) was dissolved in tetrahydrofuran (20 ml). At −78° C., a hexane solution (1.60M, 11.4 ml, 18.2 mmol) of n-butyl lithium was added dropwise to the resulting solution. The reaction mixture was stirred at the same temperature for 30 minutes, followed by the dropwise addition of a tetrahydrofuran solution (20 ml) of 4-fluorobenzonitrile (2.00 g, 16.5 mmol). After stirring further at the same temperature for 30 minutes, N,N-dimethylformamide (1.7 ml, 21.5 mmol) was added dropwise to the reaction mixture. At the same temperature, the reaction mixture was stirred for 10 minutes. To the reaction mixture were added acetic acid and a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel chromatography. The fraction obtained from the n-hexane:ethyl acetate=10:2 eluate was concentrated under reduced pressure to give the title compound (1.83 g, 12.3 mmol, 74%) as a pale yellowish brown oil.

1. stirringAfter stirring further at the same temperature for 30 minutes
2. stirringAt the same temperature, the reaction mixture was stirred for 10 minutes
3. extractiona saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. customThe residue thus obtained
8. concentrationethyl acetate=10:2 eluate was concentrated under reduced pressure

ORD record

ord-f4a6ece708654a0d8971734aa8b69cac

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932271B2