Sodium hydride → HCID 15584689, compound

Temperature

0 °C

To a stirred solution of 3-mercaptobenzoic acid methyl ester (2.32 g, 13.8 mmol) in DMF (15 mL) at 0° C. was added NaH (60% dispersion in mineral oil, 608 mg, 15.2 mmol) in small portions. After stirring for 10 min at 0° C., and a further 30 min at room temperature, perfluoroisopropyl iodide (2.16 mL, 15.2 mmol, 1.1) was added to the reaction. Following the addition, the reaction was stirred for 10 min at room temperature and then heated to 60° C. After 90 min at 60° C. the reaction was cooled to room temperature, diluted with ethyl ether (150 mL), washed with brine (2×200 mL), saturated aqueous NaHCO3 (200 mL), brine (100 mL), dried over MgSO4 and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using 5% EtOAc in hexanes as an eluent to furnish 3-(1,2,2,2-tetrafluoro-1-trifluoromethylethylthio)benzoic acid methyl ester (3.13 g).

1. additionthe addition
2. stirringthe reaction was stirred for 10 min at room temperature
3. temperatureheated to 60° C
4. temperatureAfter 90 min at 60° C. the reaction was cooled to room temperature
5. washwashed with brine (2×200 mL), saturated aqueous NaHCO3 (200 mL), brine (100 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash column chromatography on silica gel using 5% EtOAc in hexanes as an eluent

ORD record

ord-4240fac3487041cdb92800e2b01f5d9b

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691843B2