Azobisisobutyronitrile → HCID 10857674, compound

HRID 2203303Notes

Reaction equation

HRID 2203303 reaction equation
[C:1]1([CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:13][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 569653Methyl alpha-methylbenzeneacetate

Product 1

HCID 10857674HCID 10857674, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A carbon tetrachloride (150 mL) solution of the intermediate from Step A (10.39 g, 66.6 mmol), N-bromosuccinimide (14.22 g, 80 mmol) and AIBN (0.547 g, 3.33 mmol) was heated to reflux. After 4 hours the reaction solution was cooled to room temperature and the mixture filtered. The filtrate was concentrated and the residue purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (500 MHz, CHCl3-d): δ 7.59-7.53 (m, 2H); 7.37-7.30 (m, 3H); 3.80 (s, 3H); 2.31 (s, 3H).

Workup

  1. filtrationthe mixture filtered
  2. concentrationThe filtrate was concentrated
  3. customthe residue purified by silica gel chromatography
  4. customto give the indicated product

Sources & evidence

ORD record
ord-cbd546dbd502495a83bc811bdc24cd69
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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