N-bromobutanimide → 3-Bromo-7-(bromomethyl)-phenanthrene

HRID 1084315Notes

Reaction equation

HRID 1084315 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH3:16])[CH:9]=3.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH2:16][Br:17])[CH:9]=3

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 151591363-Bromo-7-methylphenanthrene

Product 1

HCID 151591373-Bromo-7-(bromomethyl)-phenanthreneYield 79.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromo-7-methylphenanthrene (2.640 g, 9.736 mmol) and N-bromosuccinimide (1.733 g, 9.736 mmol) in 200 ml of carbon tetrachloride was heated to reflux and benzoyl peroxide (25 mg) was added. After 2.5 hour a starch-iodide test showed that no NBS remained and the mixture was cooled to room temperature, washed with water, dried (MgSO4) and evaporated to give 3.14 g of crude product as a solid. Flash chromatography through 330 g of silica gel (10% CH2Cl2 /hexane) gave 2.719 g of a white solid which was recrystallized from 70 ml of cyclohexane (reflux to RT) to yield 2.061 g (60%) of the title compound as a white solid, mp 147°-148° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give 3.14 g of crude product as a solid

Sources & evidence

ORD record
ord-a139d3be1bbb426c88026f08feb3c881
Source dataset
uspto-grants-1991_04
Patent number
US05004739

Reaction notes

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