Benzoyl Peroxide → HCID 10910383, compound

HRID 882148Notes

Reaction equation

HRID 882148 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])/[C:2](=[CH:4]/[CH3:5])/[CH3:3].C1C(=O)N([Br:16])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:5]/[CH:4]=[C:2](\[CH3:3])/[C:1]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5323652Methyl 2-methylcrotonate

Product 1

HCID 10910383HCID 10910383, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl tiglate (2.00 g, 17.5 mmol) in CCl4 (8.76 mL) was added NBS (3.43 g, 19.3 mmol) and benzoyl peroxide (212 mg, 0.876 mmol). The reaction was heated to reflux for 3 hours, cooled and filtered through Celite using DCM to wash the filtrate. The reaction was concentrated in vacuo and then purified by silica chromatography using 1-15% EtOAc/hexane. The product was collected and concentrated in vacuo to afford the desired product as a colorless oil that was taken on to the next step without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. filtrationfiltered through Celite
  5. washto wash the filtrate
  6. concentrationThe reaction was concentrated in vacuo
  7. custompurified by silica chromatography
  8. customThe product was collected
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-778fffb3877a40e49591b42828642c31
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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