Dimethylformamide → 1-Bromo-3,6,8-tri(4-methylnaphthalene-1-yl)pyrene

HRID 600164Notes

Reaction equation

HRID 600164 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:25]3[C:26]4=[C:27]5[C:22](=[CH:23][CH:24]=3)[CH:21]=[CH:20][C:19]([C:28]3[C:37]6[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=6)[C:31]([CH3:38])=[CH:30][CH:29]=3)=[C:18]5[CH:17]=[CH:16][C:15]4=[C:14]([C:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:42]([CH3:49])=[CH:41][CH:40]=3)[CH:13]=2)=[CH:4][CH:3]=1.[Br:50]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:50][C:21]1[C:22]2[C:27]3=[C:26]4[C:25](=[CH:24][CH:23]=2)[C:12]([C:5]2[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:13][C:14]([C:39]2[C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[C:42]([CH3:49])=[CH:41][CH:40]=2)=[C:15]4[CH:16]=[CH:17][C:18]3=[C:19]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([CH3:38])=[CH:30][CH:29]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 866285941,3,6-Tri(4-methylnaphthalene-1-yl)pyrene

Product 1

HCID 866285931-Bromo-3,6,8-tri(4-methylnaphthalene-1-yl)pyreneYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of 1.9 g of the above-mentioned 1,3,6-tri(4-methylnaphthalene-1-yl)pyrene, 0.64 g of N-bromosuccinimide and 15 ml of dimethylformamide was stirred under nitrogen gas stream at a temperature of 60° C. for 6 hours. After cooling the mixed solution to room temperature, 50 ml of water was injected thereinto to extract therefrom with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried by magnesium sulfate and thereafter concentrated by evaporation. The organic layer was purified by silica gel column chromatography and thereafter vacuum dried under a temperature of 70° C. to obtain 1.5 g of 1-bromo-3,6,8-tri(4-methylnaphthalene-1-yl)pyrene as pale-yellow powder.

Workup

  1. extractionto extract
  2. washThe organic layer was washed twice with 50 ml of water
  3. dry with materialdried by magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe organic layer was purified by silica gel column chromatography
  6. customvacuum dried under a temperature of 70° C.

Sources & evidence

ORD record
ord-ad961cfacc5549c48c88364599b9bdce
Source dataset
uspto-grants-2011_03
Patent number
US07901794B2

Reaction notes

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