Reaction #1994258

ord-385169d1f60d4714b26b893d582ccc4a

Reaction equation

c1ccc(-c2ccc(N3c4ccccc4Cc4ccccc43)cc2)cc1
10-(biphenyl-4-yl)-9,10-dihydroacridine
O=C1CC(Br)C(=O)N1
bromosuccinimide
Brc1ccc2c(c1)Cc1ccccc1N2c1ccc(-c2ccccc2)cc1
10-(biphenyl-4-yl)-2-bromo-9,10-dihydroacridine
Yield 77.7%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washthe resultant solution was washed with distilled water
  2. 2
    ExtractionThen, an organic layer was extracted
  3. 3
    Dryingdried with sodium sulfate so as
  4. 4
    Otherto remove the solvent
  5. 5
    OtherThe residue was purified by silica gel column chromatography (methylene chloride/n-hexane (1/20))

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08597802B2uspto-grants-2013_12