N-bromobutanimide → 9-Bromo-10-(4-formylphenyl)anthracene

HRID 901764Notes

Reaction equation

HRID 901764 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[C:15]([CH:16]=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:5][CH:4]=1)=[O:2].C1C(=O)N([Br:30])C(=O)C1>CN(C=O)C.O>[Br:30][C:16]1[C:17]2[C:22]([C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:8][CH:7]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 221380334-(Anthracen-9-yl)benzaldehyde

Product 1

HCID 221380459-Bromo-10-(4-formylphenyl)anthraceneYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

9-(4-Formylphenyl)anthracene (3.3 g, 12 mmole) was suspended in anhydrous DMF (40 ml). To the resultant suspension, a solution (8 ml) of NBS (2.3 g, 13 mmole, 1.1 eq) in anhydrous DMF was added and the obtained mixture was stirred at the room temperature for 10 hours and left standing for one night. After the reaction mixture was diluted with water (50 ml), the solid was separated by filtration and washed with methanol and a yellow solid (3.9 g, 90%) was obtained.

Workup

  1. waitleft
  2. waitstanding for one night
  3. customthe solid was separated by filtration
  4. washwashed with methanol

Sources & evidence

ORD record
ord-cdb4e78037f54d8fb9353e613262a9e9
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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