Sodium hydride → (2R)-4-(4-bromo-3,5-dimethylphenoxy)butan-2-ol

To 4-bromo-3,5-dimethylphenol (5.4 g) in dehydrated N,N-dimethylformamide (60 mL), sodium hydride (1.1 g) was added under ice-cooling and the resultant reaction mixture was stirred for 30 minutes. To the reaction mixture, (R)-3-hydroxybutyl 4-methylbenzenesulfonate (5.0 g) was added and the resultant reaction mixture was stirred at room temperature for 45 minutes. To the reaction mixture, a saturated ammonium chloride aqueous solution was added, followed by extracting the reaction mixture with ethyl acetate. The organic phase was washed with a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate-95:5 to 80:20) to obtain the subject compound (4.2 g) as a colorless solid.

1. temperaturecooling
2. customthe resultant reaction mixture
3. customthe resultant reaction mixture
4. stirringwas stirred at room temperature for 45 minutes
5. extractionby extracting the reaction mixture with ethyl acetate
6. washThe organic phase was washed with a saturated saline
7. dry with materialwas dried over anhydrous sodium sulfate
8. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
9. customthe resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate-95:5 to 80:20)

ORD record

ord-0d0874d47d764584ab5ea2f001759e66

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455500B2