Dimethylformamide → HCID 86101315, compound

HRID 1914423Notes

Reaction equation

HRID 1914423 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=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[Br:39]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:39][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][CH:14]=[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 86101313HCID 86101313, compound

Product 1

HCID 86101315HCID 86101315, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of 1.7 g of 1,6-di(4-methylnaphthalen-1-yl)pyrene, 0.54 g of N-bromosuccinimide and 30 ml of dimethylformamide was stirred under a nitrogen gas stream at 60° C. for 6 hours. The solution was cooled to room temperature and 50 ml of water was poured into the solution, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then concentrated by evaporation. The resulting concentrate was recrystallized from toluene and then vacuum-dried at 70° C. to obtain 1.5 g of 1-bromo-3,8-di(4-methylnaphthalen-1-yl)pyrene as a pale yellow powder.

Workup

  1. extractionfollowed by extraction with 100 ml of dichloromethane
  2. washThe organic layer was washed twice with 50 ml of water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. concentrationThe resulting concentrate
  6. customwas recrystallized from toluene
  7. customvacuum-dried at 70° C.

Sources & evidence

ORD record
ord-5ff6041567c9451092794ecb8ca61572
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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