Benzoyl Peroxide → HCID 66611712, compound

HRID 2204685Notes

Reaction equation

HRID 2204685 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13]([Br:15])[C:12]([CH3:16])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].C1C(=O)N([Br:24])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:14]=[C:13]([Br:15])[C:12]([CH2:16][Br:24])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66611339Methyl 2-(acetyloxy)-4-bromo-5-methylbenzoate

Product 1

HCID 66611712HCID 66611712, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 2-(acetyloxy)-4-bromo-5-methylbenzoate (may be prepared as described in Description 15; 705 mg, 2.46 mmol) in carbon tetrachloride (10 ml) was added NBS (437 mg, 2.46 mmol) and benzoyl peroxide (47.6 mg, 0.15 mmol). The solution was heated at 85° C. overnight, cooled and the solvent was removed in vacuo to give a residue. Purification by column chromatography (SiO2, 6:1 cyclohexane/ethyl acetate) yielded the title compound as an oil. 741 mg.

Workup

  1. temperaturecooled
  2. customthe solvent was removed in vacuo
  3. customto give a residue
  4. customPurification by column chromatography (SiO2, 6:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-986932b16e5c48adafe0e93a1d9e8906
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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