Azobisisobutyronitrile → HCID 57443324, compound

HRID 2261847Notes

Reaction equation

HRID 2261847 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][CH:12]([CH3:14])[CH3:13].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:16])=[CH:6][C:5]=1[O:11][CH:12]([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 57443322HCID 57443322, compound

Product 1

HCID 57443324HCID 57443324, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-isopropoxy-4-methyl-benzoic acid methyl ester (1.00 g, 4.8 mmol), N-bromosuccinimide (0.940 g, 5.28 mmol), 2,2′-azo-bis-isobutyronitrile (50 mg, 0.30 mmol) and carbon tetrachloride (20 mL) is stirred under a bright lamp for 3 h. The mixture is concentrated and the residue is purified via flash chromatography (0 to 50% EtOAc-heptane) to provide the title compound (0.85 g, 62%) as an orange oil. ES/MS m/e 288.7 (M+1).

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is purified via flash chromatography (0 to 50% EtOAc-heptane)

Sources & evidence

ORD record
ord-8d4307b8735241879fd3a461cfb73dd4
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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