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

HRID 1907076Notes

Reaction equation

HRID 1907076 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:3][CH:2]=1.[Br:27]C1CC(=O)NC1=O>C(Cl)(Cl)Cl>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14][C:15]3[CH:16]=[C:17]([Br:27])[CH:18]=[CH:19][C:20]2=3)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 38309BromosuccinimideHCID 1872041910-(Biphenyl-4-yl)-9,10-dihydroacridine

Product 1

HCID 6752358010-(Biphenyl-4-yl)-2-bromo-9,10-dihydroacridineYield 77.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The obtained 10-(biphenyl-4-yl)-9,10-dihydroacridine (15.3 g, 45.9 mmol) was added with chloroform (500 ml), and then with bromosuccinimide (9.8 g, 55.1 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 (1/20)) to obtain 10-(biphenyl-4-yl)-2-bromo-9,10-dihydroacridine compound (white solid, 14.7 g, yield 77%).

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 (1/20))

Sources & evidence

ORD record
ord-385169d1f60d4714b26b893d582ccc4a
Source dataset
uspto-grants-2013_12
Patent number
US08597802B2

Reaction notes

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