N-bromobutanimide → Bromo-tert-butylpyrene

HRID 656849

Reaction equation

HRID 656849 reaction equation
[C:1]([C:5]1[C:18]2[C:19]3=[C:20]4[C:15](=[CH:16][CH:17]=2)[CH:14]=[CH:13][CH:12]=[C:11]4[CH:10]=[CH:9][C:8]3=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:28])C(=O)C1>COCCOC>[Br:28][C:6]1[CH:7]=[C:8]2[C:19]3=[C:20]4[C:15]([CH:14]=[CH:13][CH:12]=[C:11]4[CH:10]=[CH:9]2)=[CH:16][CH:17]=[C:18]3[C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 187956Pyrene, 1-(1,1-dimethylethyl)-2×

Product 1

HCID 86639773Bromo-tert-butylpyreneYield 90%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

Next, 25.0 g (0.10 mol) of tert-butylpyrene and 250 ml of DME (1,2-dimethoxyethane) were charged in a reaction vessel, and the mixture was cooled to 0° C. Next, NBS was added in an amount of 4 equivalents relative to tert-butylpyrene, and the resulting mixture was stirred overnight at room temperature, filtered, and recrystallized to produce 29.5 g of bromo-tert-butylpyrene crystals in a yield of 90%.

Workup

  1. filtrationfiltered
  2. customrecrystallized

Sources & evidence

ORD record
ord-5f32d15fadfa4e929daf62d905b40864
Source dataset
uspto-grants-2011_12
Patent number
US08071993B2

Linked notes

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