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

Temperature

0 °C

Dissolve 4bromo-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 record

ord-23ac74d0b8544077a282fa95cd95edf8

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585977B2