Bromoform → 1,1-Dibromo-2,2-diphenylcyclopropane

HRID 1247698Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9]C=1.CCCCCC.[CH:27]([Br:30])(Br)[Br:28]>O>[Br:28][C:27]1([Br:30])[CH2:1][C:14]1([C:13]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:7]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: -5 °C

Procedure

Under a nitrogen atmosphere, potassium tert-butoxide (14.8 g, 132 mmol), diphenylethylene (13.2 g, 73.3 mmol) and hexane (75 ml) were placed in a reaction flask and cooled to −5° C. To this, bromoform (24.1 ml, 95.4 mmol) was added gradually, and the mixture was stirred at the same temperature for 30 minutes. Then, water was added to the reaction mixture and the organic layer was extracted with toluene. The toluene extract was dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure. The residue was recrystallized from a mixed solvent of isopropanol and toluene to give the title compound (14.4 g, 56%) as white crystal.

Workup

extractionthe organic layer was extracted with toluene
extractionThe toluene extract
dry with materialwas dried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue was recrystallized from a mixed solvent of isopropanol and toluene

Sources & evidence

ORD record: ord-62337468c5a54a979fd8db2e2325261b
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129367B2

Reaction notes

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