Water → 1-Bromo-4-(propan-2-ylsulfanyl)benzene

Temperatur

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 (153 mg, 6.4 mmol) in portions. After the vigorous gas evolution stops, add 2-bromo-propane (0.60 mL, 6.4 mmol) and stir the reaction overnight at room temperature. Slowly pour the reaction into water (300 mL) and extract with ethyl acetate (2×150 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 5% ethyl acetate in hexanes to yield 1.1 g of 1-bromo-4-isopropylsulfanyl-benzene (92%).

1. customthe reaction overnight at room temperature
2. additionSlowly pour
3. extractionextract with ethyl acetate (2×150 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-Eintrag

ord-6d9b2a5e1cd8485db7ad31022b22b145

Quelldatensatz

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07399867B2