Benzoyl Peroxide → Acetic acid, 2-[4-(bromomethyl)phenoxy]-, methyl ester

HRID 2170625Notes

Reaction equation

HRID 2170625 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:14][CH2:13][C:1]1[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 601946Methyl (p-tolyloxy)acetate

Product 1

HCID 67049717Acetic acid, 2-[4-(bromomethyl)phenoxy]-, methyl esterYield 56.1%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the methyl 2-(p-tolyloxy)acetate (3.10 g, 17.2 mmol) in carbon tetrachloride (60 mL) was added N-bromosuccinimide (3.57 g, 20 mmol) followed by benzoyl peroxide (463 mg, 1.9 mmol). The resulting solution was heated at reflux overnight, and then diluted with methylene chloride. The mixture was washed with brine, dried on MgSO4, and concentrated. The resulting colorless oil was purified by chromatography on silica gel (Hexane/ethyl acetate 9/1) to afford a colorless oil (2.5 g, 56%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with brine
  4. customdried on MgSO4
  5. concentrationconcentrated
  6. customThe resulting colorless oil was purified by chromatography on silica gel (Hexane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-4d22a07da7114d3292508437d08fb0b4
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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