Water → HCID 18628390, compound

HRID 2354524Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:13]1([C:19]2[C:32]3[C:23](=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][CH:26]=[N:25]4)[N:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C1COCC1>[C:2]1([C:26]2[CH:27]=[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:29]3[C:24](=[C:23]4[C:32](=[CH:31][CH:30]=3)[C:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:20][CH:21]=[N:22]4)[N:25]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a three-necked flask of 250 ml, 0.97 g (6.16 mmol) of bromobenzene and 70 ml of THF were charged, then 3.9 ml (22 mmol) n-butyllithium (1.6M in Hexane solution) was dropped under stirring at −78° C. in a nitrogen atmosphere. The mixture was stirred for one hour at −78° C., and a solution of 1.86 g (5.6 mmol) 4,7-diphenyl-1,10-phenanthroline in 30 ml THF was dropped. Then the mixture was stirred at room temperature for overnight and was added with water. The organic layer was extracted with Dichloromethane and dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation. The product was purified by column chromatography on alumina using Dichloromethane/Hexane as eluent and dried in vacuo, obtaining white powder compound 0.85 g (yield of 37.21%).

Workup

stirringThe mixture was stirred for one hour at −78° C.
stirringThen the mixture was stirred at room temperature for overnight
extractionThe organic layer was extracted with Dichloromethane
dry with materialdried with anhydrous magnesium sulfate
customthe solvent was removed by rotary evaporation
customThe product was purified by column chromatography on alumina
customdried in vacuo

Sources & evidence

ORD record: ord-05283814fd1d4e4cb7b3d5a0b2e9aa1f
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754348B2

Reaction notes

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