Dimethylformamide → 2-Fluoro-4-methoxybenzaldehyde

To a solution of 1-bromo-2-fluoro-4-methoxybenzene (3.02 g) in tetra hydrofuran (75 mL) was added n-butyl lithium (2.71 mol/L n-hexane solution, 6.0 mL) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To this mixture was added N,N-dimethylformamide (1.7 mL) at the same temperature, and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with diethyl ether. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=8/1-4/1) to give 2-fluoro-4-methoxybenzaldehyde (1.54 g). The title compound was prepared in a similar manner to that described in Reference Example 45 using this material instead of 4-isobutylbenzaldehyde.

1. stirringthe mixture was stirred under ice-
2. temperaturecooling for 1 hour
3. extractionthe resulting mixture was extracted with diethyl ether
4. washThe extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was removed under reduced pressure
7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=8/1-4/1)

ORD record

ord-019df7d278a4427d92079c4e3e22c3bc

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07750145B2