N-bromobutanimide → Methyl 3-(bromomethyl)-4-methoxybenzoate

HRID 1454954Notes

Reaction equation

HRID 1454954 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH3:13].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[O:2][CH3:1])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12544789Methyl 4-methoxy-3-methylbenzoate

Product 1

HCID 23158763Methyl 3-(bromomethyl)-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 4-methoxy-3-methylbenzoate (10.0 g, 55.6 mmol) dissolved in CCl4 (500 mL) was added N-bromosuccinimide (10.8 g, 61.1 mmol) and benzoyl perioxide (1.30 g, 5.56 mol). The mixture was irradiated with a sunlamp (250 W) to create a gentle reflux. After 2 hours of exposure the reaction was complete by TLC. The reaction mixture was cooled, filtered through celite, and concentrated to yield a white solid.

Workup

  1. customThe mixture was irradiated with a sunlamp (250 W)
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customto yield a white solid

Sources & evidence

ORD record
ord-08984ffe2cc748b0a5e8765366317131
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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