4,4'-Dichlorobenzophenone → 6,6-Di(p-chlorophenyl)fulvene

Temperature

0 °C

A reaction vessel equipped with a dropping funnel was charged with 40 ml of dehydrated tetrahydrofuran and 2.15 ml (25.9 mmol) of cyclopentadiene under a nitrogen atmosphere. Then, 18.0 mL (28.5 mmol) of a 1.58 mol/L hexane solution of n-butyllithium was slowly added dropwise while cooling this solution to 0° C., and the mixture was stirred. Subsequently, the dropping funnel was charged with a solution prepared by dissolving 5.00 g (19.9 mmol) of 4,4′-dichlorobenzophenone in 30 ml of dehydrated tetrahydrofuran was placed in. The solution was slowly added dropwise while cooling to −0° C. Thereafter, the mixture was left to stand and the temperature thereof was returned to room temperature. The mixture was then stirred for one day. This reaction solution was subjected to extraction with diethyl ether. The organic layer was washed with 1 N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated brine. The organic phase collected by separation was dried over anhydrous magnesium sulfate. Subsequently, magnesium sulfate was separated by filtration, and the filtrate was subjected to distillation under reduced pressure with use of a rotary evaporator to remove the solvent. The residue was purified by using a silica gel column to obtain a target product (yield 3.37 g (57%)). The target product was identified by 1H-NMR.

1. customA reaction vessel equipped with a dropping funnel
2. additionSubsequently, the dropping funnel was charged with a solution
3. customprepared
4. additionThe solution was slowly added dropwise
5. temperaturewhile cooling to −0° C
6. waitThereafter, the mixture was left
7. customthereof was returned to room temperature
8. stirringThe mixture was then stirred for one day
9. extractionThis reaction solution was subjected to extraction with diethyl ether
10. washThe organic layer was washed with 1 N hydrochloric acid
11. customThe organic phase collected by separation
12. dry with materialwas dried over anhydrous magnesium sulfate
13. customSubsequently, magnesium sulfate was separated by filtration
14. distillationthe filtrate was subjected to distillation under reduced pressure with use of a rotary evaporator
15. customto remove the solvent
16. customThe residue was purified
17. customto obtain a target product (yield 3.37 g (57%))

ORD record

ord-65ffb852d5d949239f76138c0c68d4e5

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382356B2