Sodium hydride → Butanoic acid, 2-(4-bromo-2-nitrophenoxy)-2-methyl-, ethyl ester

To a solution of ethyl 2-hydroxy-2-methylbutyrate (3.5 g) in tetrahydrofuran (80 ml) was added under ice-cooling sodium hydride (1.2 g), and the mixture was stirred at room temperature for 10 minutes. To the mixture was added a drop of 15-crown-5, and further thereto was added dropwise 5-bromo-2-fluoronitrobenzene (2.8 ml), and the mixture was stirred at room temperature for 14 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was 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=15/1) to give the title compound (5.5 g).

1. stirringthe mixture was stirred at room temperature for 14 hours
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

ORD record

ord-9c6346f3b36c4374af5317d7bcdc962b

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389511B2