Azobisisobutyronitrile → Methyl 4-(bromomethyl)-3-methoxybenzoate

HRID 906102Notes

Reaction equation

HRID 906102 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl ester

Product 1

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateYield 97.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 4-methyl-3-(methyloxy)benzoate (1.00 g, 5.55 mmol), N-bromosuccinimide (1.09 g, 6.10 mmol) and a catalytic amount of 2,2′-azobis(isobutyronitrile) (AIBN) was refluxed in carbon tetrachloride (40 ml) for 16 h. The reaction mixture was filtered and the solution was washed with brine (25 ml), dried over sodium sulfate and concentrated to give methyl 4-(bromomethyl)-3-(methyloxy)benzoate (1.4 g, 97% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solution was washed with brine (25 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1e75a604aa444ac8bc6c2431c2a218ce
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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