Toluene → HCID 86709913, compound

HRID 1482176Notes

Reaction equation

HRID 1482176 reaction equation
[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:6]=[CH:5][C:4]([N:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]4([C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:10]=3[CH:9]=2)=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[Br:52]N1C(=O)CCC1=O>C(OCC)(=O)C>[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:2]=[CH:3][C:4]([N:7]([C:33]2[CH:34]=[CH:35][C:36]([Br:52])=[CH:37][CH:38]=2)[C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]4([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=5[C:27]5[C:32]4=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:10]=3[CH:9]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 86709914HCID 86709914, compound

Product 1

HCID 86709913HCID 86709913, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL three-neck flask were added 3.0 g (5.4 mmol) of N-(1,1′-biphenyl-4-yl)-N-phenyl-9,9′-spirobi[9H-fluoren]-2-amine, 20 mL of toluene, and 40 mL of ethyl acetate. To the solution was added 0.93 g (5.2 mmol) of N-bromosuccinimide (abbreviation: NBS), and the mixture was stirred for 25 hours. After the stirring, the mixture was washed with water and a saturated aqueous solution of sodium hydrogen carbonate, and then the organic layer was dried over magnesium sulfate. This mixture was separated by gravity filtration, and the filtrate was concentrated to give a solid. This solid was purified by silica gel column chromatography. In the column chromatography, hexane and then toluene:hexane=1:5 were used as developing solvents. The resulting fraction was concentrated to give a solid. The obtained solid was recrystallized from ethyl acetate/hexane to give 2.8 g of a white solid in a yield of 83%.

Workup

  1. washAfter the stirring, the mixture was washed with water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and then the organic layer was dried over magnesium sulfate
  3. customThis mixture was separated by gravity filtration
  4. concentrationthe filtrate was concentrated
  5. customto give a solid
  6. customThis solid was purified by silica gel column chromatography
  7. concentrationThe resulting fraction was concentrated
  8. customto give a solid
  9. customThe obtained solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ddfba77a6fc346f09b452b83140699b1
Source dataset
uspto-grants-2016_08
Patent number
US09412962B2

Reaction notes

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