2,7-Dibromo-9-fluorenone → 9-(2-Biphenylyl)-2,7-dibromo-9-fluorenol

HRID 600101

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1>C(OCC)C>[C:11]1([C:12]2[CH:4]=[CH:3][CH:2]=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:5]1([OH:16])[C:4]2[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=2

Participants

Conditions

Temperature: 50 °C

Procedure

15.2 g (45 mmol) of 2,7-dibromo-9-fluorenone was put in a 100 mL three-necked flask, and nitrogen substitution was conducted. 40 mL of diethyl ether was added. The Grignard reagent above was transferred into a dropping funnel by a cannula so as not to expose it to the atmosphere, and was added dropwise into the mixture. The mixture was refluxed at 50° C. After the reaction, the solution was washed with water. Then the aqueous layer was extracted with ethyl acetate and combined with the organic layer. The layers were washed with a saturated saline solution, then dried with magnesium sulfate. Filtration and concentration were carried out, and 22 g of 9-(biphenyl-2-yl)-2,7-dibromo-9-fluorenol was obtained as a white solid, in a yield of 90%.

Workup

additionwas added dropwise into the mixture
customAfter the reaction
washthe solution was washed with water
extractionThen the aqueous layer was extracted with ethyl acetate
washThe layers were washed with a saturated saline solution
dry with materialdried with magnesium sulfate
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-7644fd9bc8b649949e93ad86085126fa
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897964B2

Linked notes

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