Benzoyl Peroxide → HCID 86682096, compound

HRID 1750023Notes

Reaction equation

HRID 1750023 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1[CH3:13].[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:4]1[C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=[CH:12][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 89420359HCID 89420359, compound

Product 1

HCID 86682096HCID 86682096, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 6-methoxy-7-methylbenzofuran-3(2H)-one (0.670 g, 3.76 mmol) in carbon tetrachloride (38 mL) was added with N-bromosuccinimide (0.737 g, 4.14 mmol) and benzoyl peroxide (0.0456 g, 0.188 mmol), and the mixture was refluxed for 4 hours by heating. The reaction mixture was cooled to room temperature, and then filtered, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 7-(bromomethyl)-6-methoxybenzofuran-3(2H)-one (0.411 g, 42%).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureby heating
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-d5868115bb3242bc923d7525240a809f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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