Benzoic acid, 4-ethyl-, methyl ester → Methyl 4-(1-bromoethyl)benzoate

HRID 1654720

Reaction equation

HRID 1654720 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH3:2].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C1C(C(OOOC(=O)C2C=CC=CC=2)=O)=CC=CC=1>[Br:13][CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 23827Benzoic acid, 4-ethyl-, methyl esterHCID 67184N-bromobutanimide

Product 1

HCID 12342351Methyl 4-(1-bromoethyl)benzoateYield 109.2%

Reagents, catalysts & solvents 2

HCID 53400210Perbenzoic anhydrideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 4-ethylbenzoate (5.12 g) in carbon tetrachloride (50 ml) were added perbenzoic anhydride (0.20 g) and N-bromosuccinimide (6.07 g) in turn, and the mixture was heated and refluxed. After 30 minutes, the mixture was allowed to cool, and the precipitate was separated by filtration, and washed with carbon tetrachloride. The filtrate and the washings were combined, and concentrated under reduced pressure to give the title compound (8.28 g)

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed
  3. temperatureto cool
  4. customthe precipitate was separated by filtration
  5. washwashed with carbon tetrachloride
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-56ee622df6874019bb4d51d01fee57fe
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Linked notes

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