1,2-Dibromoethane → 9,9-Bis(3-bromophenyl)-9H-fluorene

62.9 g (270 mmol) of 2-bromobiphenyl mixed with 400 ml of THF, 550 ml of toluene, 45 ml of 1,2-dimethoxyethane and 2.6 ml of 1,2-dibromoethane are reacted with 6.6 g (250 mmol) of magnesium to give the corresponding Grignard compound. A solution of 60.0 g (176 mmol) of bis(3-bromophenyl) ketone in 600 ml of THF is added dropwise to the cooled Grignard solution. When the addition is complete, the reaction mixture is heated under reflux for 4 h, the solvent is then removed in vacuo, the residue is dissolved in 700 ml of glacial acetic acid, 10 ml of hydrogen bromide in 30% glacial acetic acid are added, and the mixture is heated under reflux for 6 h. After cooling with stirring, the precipitated solid is filtered off with suction, washed twice with 200 ml of glacial acetic acid each time and three times with 300 ml of ethanol each time and then dried in vacuo. Yield: 69.0 g (145 mmol), 82.1%, 99% pure according to 1H-NMR.

1. customto give the corresponding Grignard compound
2. additionWhen the addition
3. temperaturethe reaction mixture is heated
4. temperatureunder reflux for 4 h
5. customthe solvent is then removed in vacuo
6. dissolutionthe residue is dissolved in 700 ml of glacial acetic acid
7. addition10 ml of hydrogen bromide in 30% glacial acetic acid are added
8. temperaturethe mixture is heated
9. temperatureunder reflux for 6 h
10. temperatureAfter cooling
11. filtrationthe precipitated solid is filtered off with suction
12. washwashed twice with 200 ml of glacial acetic acid each time and three times with 300 ml of ethanol each time
13. customdried in vacuo

ORD-Eintrag

ord-7fce24a651ee49c0bfa4055cbc1c9a2e

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09416310B2