Dimethylformamide → 1-Bromo-6-(2-naphthyl)pyrene

HRID 1027314Notes

Reaction equation

HRID 1027314 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:24]2[C:25]3=[C:26]4[C:21](=[CH:22][CH:23]=2)[CH:20]=[CH:19][CH:18]=[C:17]4[CH:16]=[CH:15][C:14]3=[CH:13][CH:12]=1.[Br:27]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:27][C:18]1[C:17]2[C:26]3=[C:25]4[C:14](=[CH:15][CH:16]=2)[CH:13]=[CH:12][C:11]([C:2]2[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=2)=[C:24]4[CH:23]=[CH:22][C:21]3=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 540473501-(2-Naphthyl)pyrene

Product 1

HCID 581615471-Bromo-6-(2-naphthyl)pyreneYield 21.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Next, a mixed solution of 7.5 g of 1-(2-naphthyl)pyrene, 4.1 g of N-bromosuccinimide and 115 ml of dimethylformamide was heated with stirring under a nitrogen gas flow at 50° C. for 7.5 hours. After cooling the solution to room temperature, 100 ml of water was injected, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration, washed twice with 100 ml of water and then washed twice with 100 ml of methanol. The solid was washed three times with 50 ml of 1,2-dimethoxyethane and then vacuum-dried to obtain 2.0 g of 1-bromo-6-(2-naphthyl)pyrene.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. stirringby stirring at room temperature for 0.5 hours
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed twice with 100 ml of water
  5. washwashed twice with 100 ml of methanol
  6. washThe solid was washed three times with 50 ml of 1,2-dimethoxyethane
  7. customvacuum-dried

Sources & evidence

ORD record
ord-65aec94700a44cc4a40d3f58ac8d0de9
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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