N-bromobutanimide → 1-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

Temperature

85 °C

Dissolve 4-chloro-1-(4-isopropyl-phenyl)-butan-1-one (5.00 g, 22.2 mmol) and N-bromosuccinimide (4.1 g, 23.0 mmol) in carbon tetrachloride (25 mL) and add AIBN radical initiator (300 mg). Stir and maintain under a nitrogen atmosphere at 80-90° C. or optionally irradiate with a sunlamp until a vigorous exotherm occurs at which point momentarily remove until reflux subsides and then reapply the heat. Reflux for 30 minutes and add another potion of N-bromosuccinimide (100 mg) while maintaining reflux and reflux an additional 15 minutes. Cool to room temperature and precipitate the succinimide from the solution by allowing to stand overnight. Filter and wash the succinimide (2.25 g) with carbon tetrachloride (20 mL). Combine the filtrates and evaporate the solvent in vacuo to give the title compound as a yellow oil (6.80 g, 100%).

1. customoptionally irradiate with a sunlamp until a vigorous exotherm
2. custommomentarily remove
3. temperatureuntil reflux subsides
4. temperatureReflux for 30 minutes
5. additionadd another potion of N-bromosuccinimide (100 mg)
6. temperaturewhile maintaining
7. temperaturereflux
8. temperaturereflux an additional 15 minutes
9. temperatureCool to room temperature
10. customprecipitate the succinimide from the solution
11. filtrationFilter
12. washwash the succinimide (2.25 g) with carbon tetrachloride (20 mL)
13. customCombine the filtrates and evaporate the solvent in vacuo

ORD record

ord-995e3d6976de4b818da0a55f60a693e4

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06479663B2