Ethanol → Ethyl 4-bromo-2-methylbenzoate

HRID 1893575Notes

Reaction equation

HRID 1893575 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22616358Ethyl 4-bromo-2-methylbenzoateYield 93%

Procedure

4-Bromo-2-methylbenzoic acid (9.97 g, 46.4 mmol) and concentrated sulfuric acid (1.0 ml) were dissolved in ethanol (170 ml), and the mixture was heated under reflux for 33 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with an ethyl acetate-hexane=1:1 mixed solvent, washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (10.5 g, yield 93%) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 33 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with an ethyl acetate-hexane=1:1 mixed solvent
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb7f3a0c287d49fe9ecc886ca46460ba
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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