Benzoyl Peroxide → 2-(Bromomethyl)-1,3-thiazole-4-carbonitrile

Temperature

95 °C

To a mixture of 2-methyl-thiazole-4-carbonitrile (3.0 g, 24.1 mmol), N-bromosuccinimide (4.3 g, 24.1 mmol) in CCl4 (50 mL) was added benzoyl peroxide (0.583 g, 0.10 mmol). The resulting mixture was stirred at 95° C. for 15 h, concentrated under reduced pressure, diluted with EtOAc (100 mL) and washed with saturated Na2S2O3 (50 mL), NaHCO3 (50 mL) and brine (20 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The crude residue was purified via silica gel column chromatography using EtOAc/n-hexane as eluent to afford the title compound (4.6 g, 83%) as yellow oil. Rf0.39 (silica gel,EtOAc/hexane,3/7).

1. concentrationconcentrated under reduced pressure
2. additiondiluted with EtOAc (100 mL)
3. washwashed with saturated Na2S2O3 (50 mL), NaHCO3 (50 mL) and brine (20 mL)
4. dry with materialThe organic phase was dried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe crude residue was purified via silica gel column chromatography

ORD record

ord-da2c17d3fba14578967fcb9470ea9700

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07019019B2