Bromosuccinimide → 10-(Biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridine

HRID 1907078Notes

Reaction equation

HRID 1907078 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([N:7]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C:13]3[CH:12]=[C:11]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:10]=[CH:9][C:8]2=3)=[CH:3][CH:2]=1.[Br:33]C1CC(=O)NC1=O>C(Cl)(Cl)Cl>[C:1]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:6]=[CH:5][C:4]([N:7]2[C:8]3[C:13](=[CH:12][C:11]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:10][CH:9]=3)[CH2:14][C:15]3[CH:16]=[C:17]([Br:33])[CH:18]=[CH:19][C:20]2=3)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 38309BromosuccinimideHCID 6752353010-(Biphenyl-4-yl)-2-phenyl-9,10-dihydroacridine

Product 1

HCID 6752348010-(Biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridineYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10-(biphenyl-4-yl)-2-phenyl-9,10-dihydroacridine (7.8 g, 19.0 mmol) was added with chloroform (300 ml), and with bromosuccinimide (3.7 g, 21.0 mmol). The resultant solution was stirred at room temperature for 2 hours. After the reaction was completed, the resultant solution was washed with distilled water. Then, an organic layer was extracted and dried with sodium sulfate so as to remove the solvent. The residue was purified by silica gel column chromatography (methylene chloride/n-hexane (1/10)) to obtain 10-(biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridine compound (pale yellow solid, 6.5 g, yield 70%).

Workup

  1. washthe resultant solution was washed with distilled water
  2. extractionThen, an organic layer was extracted
  3. dry with materialdried with sodium sulfate so as
  4. customto remove the solvent
  5. customThe residue was purified by silica gel column chromatography (methylene chloride/n-hexane (1/10))

Sources & evidence

ORD record
ord-a96a6ae6207e48c5a850b724648051a9
Source dataset
uspto-grants-2013_12
Patent number
US08597802B2

Reaction notes

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