Water → Methyl 2-(2,2,2-trifluoroethylthio)benzoate

温度

0 °C

Methylthiosalicylate (5.0 mL, 36 mmol) was added dropwise to a stirred suspension of NaH (60% oil dispersion, 1.43 g, 36 mmol) in dry DMF (30 ml,) at room temperature. The mixture was stirred in the dark under Ar for 30 min and was then cooled to 0° C. and treated with a solution of 1,1,1-trifluoro-2-iodoethane (3.0 mL, 30 mmol) in DMF (10 mL) via cannula. The reaction flask was covered with foil and was allowed to warm to room temperature while stirring overnight. Water was poured into the mixture which was then extracted with ether (3×150 mL). The combined ether extracts were washed with saturated aqueous Na2CO3 and brine, dried over MgSO4 filtered and concentrated in vacuo. Silica gel chromatography (isocratic elution with 10% EtOAc-hexanes) afforded the title compound as a pale yellow oil:

1. temperatureto warm to room temperature
2. stirringwhile stirring overnight
3. extractionwas then extracted with ether (3×150 mL)
4. washThe combined ether extracts were washed with saturated aqueous Na2CO3 and brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. washSilica gel chromatography (isocratic elution with 10% EtOAc-hexanes)

ORDレコード

ord-e8001bdbaab44fd483d300117c45779d

出典データセット

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06387911B1