Benzoyl Peroxide → Methyl 2-bromo-2-(4-chlorophenyl)acetate

HRID 1241471Notes

Reaction equation

HRID 1241471 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH:4]([Br:13])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 104196Methyl 4-chlorophenylacetate

Product 1

HCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetateYield 81.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-chlorophenylacetic acid methyl ester (14.6 g, 79.1 mmol), N-bromosuccinimide (14.4 g, 80.7 mmol), and benzoyl peroxide (1.91 g, 7.89 mmol) in carbon tetrachloride (100 mL) was heated at reflux for 3 h. After the mixture was cooled at room temperature, hexanes (500 mL) was added. The reaction mixture was filtered and the solvent was evaporated in vacuo. The crude material was purified by column chromatography on silica (EtOAc/Hexanes, 15:85) to give the title compound as colorless oil (16.9 g, 63%): 1H NMR (400 MHz, CDCl3) δ 3.81 (s, 3H, CH3), 5.34 (s, 1H, CH), 7.44 (dd, J=60.4 Hz, J=8.4 Hz, 4H, ArH).

Workup

  1. temperatureat reflux for 3 h
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was evaporated in vacuo
  4. customThe crude material was purified by column chromatography on silica (EtOAc/Hexanes, 15:85)

Sources & evidence

ORD record
ord-bdaed6b0b9704044994a28b5693da28a
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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