Triethylamine → HCID 90418312, compound

Temperature

0 °C

Into a 100-mL round-bottom flask, was placed [4-(4-chlorophenyl)-2-(trifluoromethyl)thiophen-3-yl]methanol (500 mg, 1.71 mmol, 1.00 equiv), triethylamine (521 mg, 5.15 mmol, 3.01 equiv), dichloromethane (10.0 mL). This was followed by the addition of MsCl (390 mg, 3.42 mmol, 2.00 equiv) dropwise with stirring at 0° C. The resulting solution was stirred for 0.5 h at 25° C. The reaction progress was monitored by TLC(ethyl acetate/petroleum ether=1:6). The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×15 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 675 mg of [4-(4-chlorophenyl)-2-(trifluoromethyl)thiophen-3-yl]methyl methanesulfonate as a light yellow solid. The crude could be used for the next step directly. Mass spectrum (ESI, m/z): Calcd. for C13H10C1F3O3S2, 371.0 (M+H). found 371.0.

1. customInto a 100-mL round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 0.5 h at 25° C
3. customThe reaction was then quenched by the addition of 10 mL of water
4. extractionThe resulting solution was extracted with 3×15 mL of dichloromethane
5. washThe resulting mixture was washed with 2×20 mL of sodium chloride
6. dry with materialThe mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. customThis resulted in 675 mg of [4-(4-chlorophenyl)-2-(trifluoromethyl)thiophen-3-yl]methyl methanesulfonate as a light yellow solid

ORD record

ord-94c6b89da2dd472f84a733f177ce1ad3

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1