Benzoyl Peroxide → Methyl bromo(4-bromophenyl)acetate

HRID 1501253Notes

Reaction equation

HRID 1501253 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 316783Methyl 2-(4-bromophenyl)acetate

Product 1

HCID 12717577Methyl bromo(4-bromophenyl)acetateYield 98.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
77 °C

Procedure

To a solution of methyl 2-(4-bromophenyl)acetate (9 g, 39.5 mmol) in carbon tetrachloride was added N-bromosuccinimide (7.1 g, 40 mmol), benzoyl peroxide (1.2 g, 6.7 mmol). The mixture was heated to reflux, and then stirred at the 77° C. for 4 hours. Thin layer chromatography showed full conversion. Then the mixture was concentrated under vacuum. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20/1) to give methyl 2-bromo-2-(4-bromophenyl)acetate (12 g, 91%). 1H NMR (300 MHz, CDCl3) δ 7.68-7.65 (m, 2H), 7.52-7.49 (m, 2H), 5.35-5.31 (m, 1H), 3.89 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationThen the mixture was concentrated under vacuum
  4. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-3291aca6fbb34f2cb851314936a068b6
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…