Benzoyl Peroxide → 7-bromomethylbenzofuran-3(2H)-one

HRID 1749936Notes

Reaction equation

HRID 1749936 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[C:10]2[O:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 126327-Methylbenzofuran-3(2H)-oneHCID 67184N-bromobutanimide

Product 1

HCID 601557897-bromomethylbenzofuran-3(2H)-oneYield 49%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 7-methylbenzofuran-3(2H)-one (0.759 g, 5.12 mol) in carbon tetrachloride (50 mL) was added with N-bromosuccinimide (1.00 g, 5.63 mmol) and benzoyl peroxide (0.0830 g, 0.256 mmol), and the mixture was refluxed for 4 hours by heating. The reaction mixture was cooled to room temperature, and then filtered, and the resulting filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 7-bromomethylbenzofuran-3(2H)-one (0.573 g, 49%).

Workup

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

Sources & evidence

ORD record
ord-86434c2654e24d37b65fccdd05a66b22
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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