Benzoyl Peroxide → HCID 86681918, compound

HRID 1749722Notes

Reaction equation

HRID 1749722 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[C:6]2[O:10][CH2:9][C:8](=[O:11])[C:7]=2[CH:12]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:5]1[C:6]2[O:10][CH2:9][C:8](=[O:11])[C:7]=2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 86681917HCID 86681917, compound

Product 1

HCID 86681918HCID 86681918, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The synthesis was performed with reference to the known literature (Bioconjugate Chemistry, Vol. 18, p. 275, 2007). A solution of 5-methoxy-7-methylbenzofuran-3(2H)-one (0.25 g, 1.4 mmol) in carbon tetrachloride (15 mL) was successively added with N-bromosuccinimide (0.27 g, 1.5 mmol), and benzoyl peroxide (0.025 g, 0.070 mmol), and the mixture was refluxed for 2 hours by heating. The solid in the reaction mixture was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (75:25)) to obtain 7-(bromomethyl)-5-methoxybenzofuran-3(2H)-one (0.040 g, 11%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureby heating
  3. customThe solid in the reaction mixture was removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. washThe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (75:25))

Sources & evidence

ORD record
ord-885c172401fd4821aec3b1dafe0f7363
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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