Carbon Tetrachloride → Pyridine, 2-(bromomethyl)-5-(2,2,2-trifluoroethoxy)-

Temperatur

80 °C

Add 2-methyl-5-(2,2,2-trifluoroethoxy)-pyridine (2.5 g, 13.1 mmol), NBS (2.3 g, 13.1 mmol) and benzoyl peroxide (50 mg) to a flask containing carbon tetrachloride (30 mL). Heat the mixture at 80° C. in a sealed flask for 16 h. Cool the flask, add NBS (1.1 g, 6.5 mmol) and benzoyl peroxide (100 mg), then continue heating at 80° C. for an additional 5 h. Cool the mixture, dilute with DCM, then wash with saturated sodium bisulfite (10 mL). Collect the organic layer and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to obtain the desired intermediate (460 mg, 13%).

1. temperatureCool the flask
2. temperaturecontinue heating at 80° C. for an additional 5 h
3. temperatureCool the mixture
4. washwash with saturated sodium bisulfite (10 mL)
5. customCollect the organic layer
6. concentrationconcentrate in vacuo
7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

ORD-Eintrag

ord-674dfd0ba1844542866a3eaa2c56b8ac

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08580780B2