Benzoyl Peroxide → Methyl 2-(acetyloxy)-5-bromo-4-(bromomethyl)benzoate

HRID 2204675Notes

Reaction equation

HRID 2204675 reaction equation
C1C(=O)N([Br:8])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]([O:30][C:31]1[CH:40]=[C:39]([CH3:41])[C:38]([Br:42])=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])(=[O:29])[CH3:28]>C(Cl)(Cl)(Cl)Cl>[C:27]([O:30][C:31]1[CH:40]=[C:39]([CH2:41][Br:8])[C:38]([Br:42])=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66611776Methyl 2-(acetyloxy)-5-bromo-4-methylbenzoate

Product 1

HCID 66611269Methyl 2-(acetyloxy)-5-bromo-4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

NBS (0.71 g, 4.01 mmol) and benzoyl peroxide (0.07 g, 0.20 mmol) were added to a solution of methyl 2-(acetyloxy)-5-bromo-4-methylbenzoate (may be prepared as described in Description 3; 1.15 g, 4.01 mmol) in carbon tetrachloride (20 ml). The mixture was heated at reflux for 18 hours, cooled and the solvent removed in vacuo. Purification by SP4 (10-20% ethyl acetate/hexane) yielded the title compound as a pale yellow oil. 1.38 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperaturecooled
  4. customthe solvent removed in vacuo
  5. customPurification by SP4 (10-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9ebb55aa8dd94dec93ecde9ca6d82ae5
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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