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

HRID 1531915Notes

Reaction equation

HRID 1531915 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1)[CH3:2].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClCCl>[Br:14][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

5

Reactant 3

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

Product 1

HCID 10563066Ethyl 2-(3-(bromomethyl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [3-methylphenyl]acetic acid ethyl ester (5g), N-bromosuccinimide (5 g) and benzoyl peroxide (0.1 g) in dichloromethane (200 ml) was irradiated under a 500 W halogen lamp for 6 hours. The solvent was evaporated and the residue partitioned between diethyl ether and water. The organic phase was dried (MgSO4) and evaporated. Purified by chromatography eluting with 5-10% ethyl acetate in isohexane. Yield 5.14 g.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between diethyl ether and water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customPurified by chromatography
  6. washeluting with 5-10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a069ede5c390418cad67e5a7036445a8
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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