N-bromobutanimide → 9-Bromo-10-phenanthren-3-ylanthracene

HRID 879924

Reaction equation

HRID 879924 reaction equation
[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:15]2[C:16]3[C:21]([CH:22]=[C:23]4[C:28]=2[CH:27]=[CH:26][CH:25]=[CH:24]4)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:2]=1.C1C(=O)N([Br:36])C(=O)C1>C1COCC1>[Br:36][C:22]1[C:21]2[C:16]([C:15]([C:3]3[CH:2]=[CH:1][C:14]4[CH:13]=[CH:12][C:11]5[C:6]([C:5]=4[CH:4]=3)=[CH:7][CH:8]=[CH:9][CH:10]=5)=[C:28]3[C:23]=1[CH:24]=[CH:25][CH:26]=[CH:27]3)=[CH:17][CH:18]=[CH:19][CH:20]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 596295009-Phenanthren-3-ylanthracene

Product 1

HCID 596295449-Bromo-10-phenanthren-3-ylanthraceneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 g (80 mmol) of 9-phenanthren-3-ylanthracene are suspended in 300 ml of THF, 14.2 g (80 mmol) of NBS are added, and the mixture is stirred at RT for 2 h with exclusion of light. The solvent is subsequently removed in vacuo, and the residue is boiled in EtOH and recrystallised twice from dioxane, leaving 32.9 g (95%) of bromide as yellow crystals.

Workup

  1. customThe solvent is subsequently removed in vacuo
  2. customrecrystallised twice from dioxane

Sources & evidence

ORD record
ord-ca49e2514dd84347be27c4257bab1c98
Source dataset
uspto-grants-2015_03
Patent number
US08993123B2

Linked notes

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