Benzoyl Peroxide → Ethyl 2-(bromomethyl)-α-oxobenzeneacetate

HRID 1954474Notes

Reaction equation

HRID 1954474 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:5].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:5]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 11622483ETHYL 2-METHYLBENZOYLFORMATEHCID 21226206Ethyl acetate hexane

Product 1

HCID 23297128Ethyl 2-(bromomethyl)-α-oxobenzeneacetateYield 43.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of ethyl 2-methylbenzoylformate (10 g) in carbon tetrachloride (200 ml) were added N-bromosuccinimide (10 g) and 25%-hydrous benzoyl peroxide (1 g) and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled with ice-water and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to give a yellow oil. The oil was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give the desired ethyl 2-(bromomethyl)benzoylformate (6.1 g, yield: 43%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a yellow oil

Sources & evidence

ORD record
ord-4acbbdb1d41941e58102d233af6ef7db
Source dataset
uspto-grants-2000_09
Patent number
US06121476

Reaction notes

Loading…