2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Bromoacenaphthylene

To 25.4 g (107.3 mmol) of 5-bromoacenaphthene and 500 mL of dehydrated benzene, 29.2 g (128.7 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was added, and the mixture was stirred for 6 hours under heat refluxing. Furthermore, 6.0 g (26.4 mmol) of DDQ was added to the reaction mixture, and the mixture was stirred for 4 hours by heating. After allowing the resultant mixture to stand for cooling, a precipitate was filtered off and washed with chloroform. Filtrates were combined and washed with a 10% sodium hydroxide aqueous solution and water. After liquid separation, an organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was dried under reduced pressure to obtain 13.0 g (yield: 51.6%) of 5-bromoacenaphthylene as a brown solid.

1. temperatureunder heat
2. temperaturerefluxing
3. stirringthe mixture was stirred for 4 hours
4. temperatureby heating
5. temperaturefor cooling
6. filtrationa precipitate was filtered off
7. washwashed with chloroform
8. washwashed with a 10% sodium hydroxide aqueous solution and water
9. customAfter liquid separation
10. dry with materialan organic phase was dried over anhydrous sodium sulfate
11. distillationthe solvent was distilled off
12. customThe residue was dried under reduced pressure

ORD record

ord-f75f00d9d44545a295959e70f55cb421

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273002B2