Water → 1-Chloro-3-((R)-2,2,2-trifluoro-1-methylethoxymethyl)benzene

Temperature

0 °C

Under argon atmosphere, a suspension of sodium hydride (77 mg, 60 wt % oil dispersion) in N,N-dimethylformamide (2.0 ml) was cooled to 0° C., a solution of (R)-1,1,1-trifluoropropan-2-ol (213 mg) in N,N-dimethylformamide (2.0 ml) was added thereto, and the mixture was stirred for 15 minutes. Then, a solution of 1-bromomethyl-3-chlorobenzene (311 mg) in N,N-dimethylformamide (2.0 ml) was added thereto, and then the mixture was stirred at room temperature for 2.5 hours. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=1/0 to 19/1) to give the titled compound (307 mg).

1. stirringthe mixture was stirred at room temperature for 2.5 hours
2. extractionthe mixture was extracted with ethyl acetate
3. washThis organic layer was washed with a saturated aqueous solution of sodium chloride
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=1/0 to 19/1)

ORD record

ord-d36057139f1f4c4997e333649a93df93

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846746B2