Benzoyl Peroxide → Ethyl 2-(3-(bromomethyl)phenyl)acetate

HRID 1497988Notes

Reaction equation

HRID 1497988 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)[CH3:2].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:21][CH2:12][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 96574Ethyl m-tolylacetate

Product 1

HCID 10563066Ethyl 2-(3-(bromomethyl)phenyl)acetateYield 433.6%

Conditions

Temperature
70 °C

Procedure

Acetonitrile (30 mL) was degased with nitrogen for 5 minutes, and then ethyl-m-tolylacetate (2 mL, 2 mmol), NBS (1.9 g, 10.7 mmol) and benzoyl peroxide (266 mg, 1.1 mmol) were added. The resulting mixture was heated to 70° C. for 18 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine, passed through a hydrophobic frit, and the solvent was removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-50% DCM in isohexane, to provide ethyl 2-[3-(bromomethyl)phenyl]-acetate (2.23 g, 77%).

Workup

  1. customAcetonitrile (30 mL) was degased with nitrogen for 5 minutes
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed in vacuo
  4. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  5. washThe organic layer was washed with brine
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0-50% DCM in isohexane

Sources & evidence

ORD record
ord-a9aed588509b49f385049b36b5b15b23
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

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