Diisopropylamine → 6-Bromo-2-fluoro-3-(methoxymethoxy)benzaldehyde

Temperature

0 °C

A solution of diisopropylamine (364 μl) in tetrahydrofuran (1 ml) was cooled to −78° C., and thereto was added dropwise n-butyl lithium (0.86 ml, 2.77M hexane solution), and the mixture was stirred at 0° C. for 10 minutes. The reaction mixture was cooled to −78° C., and thereto was added dropwise a solution of 1-bromo-3-fluoro-4-(methoxymethoxy)benzene (470 mg) in tetrahydrofuran (1 ml), and the mixture was stirred for 30 minutes. To the mixture was added dropwise N,N-dimethyl-formamide (210 μl), and the mixture was stirred at room temperature for one hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (48 mg).

1. temperatureThe reaction mixture was cooled to −78° C.
2. stirringthe mixture was stirred for 30 minutes
3. stirringthe mixture was stirred at room temperature for one hour
4. extractionthe mixture was extracted with ethyl acetate
5. washwashed with a saturated aqueous sodium chloride solution
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-091abbf7ab8b44cda39210dc24dc45e6

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389511B2