Benzoyl Peroxide → 2,7-Dibromophenanthrene

HRID 71702

Reaction equation

HRID 71702 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C([O-])(=O)C.[K+]>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 517044Potassium AcetateHCID 28250532,7-Dibromo-9,10-dihydrophenanthrene

Product 1

HCID 111750732,7-DibromophenanthreneYield 96.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2,7-dibromo-9,10-dihydro-phenanthrene (2.4 g, 7.1 mmol), NBS (1.4 g, 7.8 mmol), and benzoyl peroxide (0.2 g) in carbon tetrachloride (300 ml) was refluxed for 2 hours. Potassium acetate (3.6 g) and acetic acid (3.2 ml) were added, and the refluxing was continued for additional 2 hours. The mixture was cooled and diluted with EtOAc. The organic phase was washed with water, saturated sodium bicarbonate, and brine, and was dried with sodium sulfate. Concentration gave 2,7-dibromo-phenanthrene (2.3 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe mixture was cooled
  3. washThe organic phase was washed with water, saturated sodium bicarbonate, and brine
  4. dry with materialwas dried with sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-534787bc3cdd4049982e4fc949cc9b0d
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Linked notes

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