Azobisisobutyronitrile → 4-(4-Methoxybenzoyl)benzyl bromide

HRID 1525311Notes

Reaction equation

HRID 1525311 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>>[Br:25][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[O:10])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 32113(4-Methoxyphenyl)(4-methylphenyl)methanone2×HCID 67184N-bromobutanimide

Product 1

HCID 131506704-(4-Methoxybenzoyl)benzyl bromide

Procedure

To a solution of (4-methoxyphenyl)(p-tolyl)methanone, 32-b. (3 g, 13.3 mmol) in CCL4 (30 ml) was added NBS (2.8 g, 16 mmol) and AIBN (50 mg), the reaction mixture was then stirred for 3 h under refluxed. The resulting mixture was cooled to ambient temperature, filtered, and filtrate was concentrated under reduce pressure. Purified by column chromatography on silica gel (petroleum ether/ethyl acetate=6:1), the pure product, 32-c, was obtained as a colorless oil (3 g, 74% yield). 1H NMR (300 MHz, DMSO-d6) δ 3.84 (s, 3H), 4.49 (s, 2H), 6.90-6.94 (m, 2H), 7.43-7.61 (m, 2H), 7.67-7.79 (m, 4H). LC-MS 305 [MH]+.

Workup

  1. temperatureunder refluxed
  2. filtrationfiltered
  3. concentrationfiltrate was concentrated
  4. customPurified by column chromatography on silica gel (petroleum ether/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-37d7e02d7eca4f30a4bb8e285612bc35
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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