Water → 1-Bromo-4-[(2,2,2-trifluoroethyl)sulfanyl]benzene

Temperature

0 °C

Dissolve 4-bromo-benzenethiol (1.0 g, 5.3 mmol) in dry dimethylformamide (50 mL) and cool to 0° C. under nitrogen. Add dry sodium hydride (152 mg, 6.4 mmol), portionwise. After the vigorous gas evolution stops, add toluene-4-sulfonic acid 2,2,2-trifluoro-ethyl ester (2.0 g, 8.0 mmol) and stir the reaction overnight at room temperature. Slowly pour the reaction into water (400 mL) and extract with ethyl acetate (2×50 mL). Wash the combined organic layers with water (100 mL) and brine (100 mL). Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Chromatograph the resultant residue on a SiO2 column with hexanes to yield 640 mg of 1-bromo-4-(2,2,2-trifluoro-ethylsulfanyl)-benzene (45%).

1. customthe reaction overnight at room temperature
2. additionSlowly pour
3. extractionextract with ethyl acetate (2×50 mL)
4. washWash the combined organic layers with water (100 mL) and brine (100 mL)
5. dry with materialDry the organic layer with sodium sulfate
6. filtrationfilter
7. concentrationconcentrate in vacuo

ORD record

ord-7b8747c0e4dd47ec82cf78abcce76db8

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399867B2