Hydrogen Bromide → 4-Bromo-4'-chloro-3-ethylbiphenyl

4′-Chloro-3-ethylbiphen-4-ylamine (14.3 g, 0.06 mol) is added to acetonitrile (143 ml) and stirred at room temperature until dissolution is complete. The reaction mixture is cooled to between −5° C. and 0° C., tert-butyl nitrite (90%, 9.8 ml, 0.074 mol) is added dropwise and the reaction mixture is maintained at between −5° C. and 0° C. for 30-40 minutes. The mixture is added slowly to a preheated (50° C.) suspension of copper (I) bromide (4.87 g, 0.034 mol) in hydrobromic acid (4.8 ml) and stirred at 50° C. for 10-15 minutes. The reaction mixture is cooled to room temperature, then poured into ice-cold water and extracted with ethyl acetate (3×500 ml). The organic extracts are washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to yield 4-bromo-4′-chloro-3-ethylbiphenyl (12 g).

1. temperatureThe reaction mixture is cooled to between −5° C. and 0° C.
2. temperaturethe reaction mixture is maintained at between −5° C. and 0° C. for 30-40 minutes
3. stirringstirred at 50° C. for 10-15 minutes
4. temperatureThe reaction mixture is cooled to room temperature
5. additionpoured into ice-cold water
6. extractionextracted with ethyl acetate (3×500 ml)
7. washThe organic extracts are washed with water
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue is purified by column chromatography on silica gel

ORD record

ord-77de59e6a0754bc59d221b505e4e887d

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828908B2