Azobisisobutyronitrile → Methyl 4-acetoxy-3-bromomethyl-5-methylbenzoate

HRID 1641995Notes

Reaction equation

HRID 1641995 reaction equation
[C:1]([O:4][C:5]1[C:14]([CH3:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH3:16])(=[O:3])[CH3:2].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:36])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[C:6]([CH3:16])=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=1[CH2:15][Br:36])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59283845HCID 59283845, compound

Product 1

HCID 59283833Methyl 4-acetoxy-3-bromomethyl-5-methylbenzoate

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

A solution of methyl 4-acetoxy-3,5-dimethylbenzoate (2.4 g) in carbon tetrachloride (35 mL) was treated with AIBN (azobisisobutrylnitrile, 0.177 g, 0.1 equivalent) and NBS (N-bromosuccinimide, 2.117 g, 1.1 equivalents). The reaction was heated at reflux under a nitrogen atmosphere for 6 h. The reaction was cooled to room temperature and diluted with chloroform (30 mL). This solution was washed with water (4×50 mL) and then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. An off-white, waxy solid was recovered. Yield=4.63 g. The crude bromide was used as such for the following reaction.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under a nitrogen atmosphere for 6 h
  3. washThis solution was washed with water (4×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customAn off-white, waxy solid was recovered
  8. customsuch for the following reaction

Sources & evidence

ORD record
ord-d54a3e1fdacd4b249a2e55a79b074e1b
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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