9-Methylphenanthrene → Phenanthrene, 9-(bromomethyl)-

HRID 868766Notes

Reaction equation

HRID 868766 reaction equation
[CH3:1][C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.C1C(=O)N([Br:23])C(=O)C1>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:23][CH2:1][C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 2

HCID 134389-MethylphenanthreneHCID 67184N-bromobutanimide

Product 1

HCID 185571Phenanthrene, 9-(bromomethyl)-Yield 89.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 9-methylphenanthrene (14.2 g, 74 mmol), benzoyl peroxide (40 mg, 0.16 mmol) and NBS (13.3 g, 74.6 mmol) in 210 mL of benzene was refluxed for 5 h. The reaction mixture was cooled to 0° C. and the succinimide precipitated was removed by filtration. The filtrate was washed by 15% NaOH, dried over MgSO4 and concentrated to yield 18 g of product which was used for the next step without further purification.

Workup

  1. temperaturewas refluxed for 5 h
  2. customthe succinimide precipitated
  3. customwas removed by filtration
  4. washThe filtrate was washed by 15% NaOH
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-089e894bbbd949f7a193802e14b14d78
Source dataset
uspto-grants-2015_03
Patent number
US08968887B2

Reaction notes

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