Ethanol → 4-(7-Bromobenz[a]anthracen-4-yl)benzaldehyde

HRID 877299Notes

Reaction equation

HRID 877299 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1[C:14]2=[C:15]3[C:24](=[CH:25][CH:26]=[C:13]2[C:12]([C:27]2[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=2)=[CH:11][CH:10]=1)[CH:23]=[C:22]1[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]1)=[CH:16]3.C(O)C>CN(C=O)C>[Br:1][C:23]1[C:24]2[C:15]([CH:16]=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[C:14]1[CH:9]=[CH:10][CH:11]=[C:12]([C:27]3[CH:28]=[CH:29][C:30]([CH:31]=[O:32])=[CH:33][CH:34]=3)[C:13]1=[CH:26][CH:25]=2

Participants

5

Reactant 3

HCID 702EthanolHCID 67184N-bromobutanimideHCID 594126624-Benz[a]anthracen-4-ylbenzaldehyde

Product 1

HCID 594125034-(7-Bromobenz[a]anthracen-4-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

29.4 g (165 mmol) of N-bromosuccinimide are added at 100° C. to a suspension of 49 g (150 mmol) of 4-benz[a]anthracen-4-ylbenzaldehyde in 800 ml of DMF. After 3 h, 500 ml of ethanol are added at room temperature, and the solid is filtered off with suction, washed with ethanol and dried. Yield: 49.3 g (119 mmol), 79%.

Workup

  1. filtrationthe solid is filtered off with suction
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-e5d66f16a7c64aedaa3166ee7d8d0186
Source dataset
uspto-grants-2015_03
Patent number
US08986852B2

Reaction notes

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