Water → 2,3-Difluoro-6-(2-methoxyethoxy)benzaldehyde

To a suspension of 2,3-difluoro-6-hydroxybenzaldehyde (0.63 g) and potassium carbonate (0.83 g) in N,N-dimethyl -formamide (4 mL) was added 2-methoxyethyl bromide (0.45 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water 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=85/15−60/40) to give 2,3-difluoro-6-(2-methoxyethoxy)benzaldehyde (0.62 g). This material was dissolved in tetrahydrofuran (6 mL). To the solution were added water (0.6 mL) and sodium borohydride (0.12 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound (0.61 g).

1. extractionthe resulting mixture was extracted with diethyl ether
2. washThe extract was washed with water and brine successively
3. dry with materialdried over anhydrous sodium sulfate
4. customThe solvent was removed under reduced pressure
5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=85/15−60/40)

ORD record

ord-797434c58249482493af4cf06f2d50ad

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040693B2