Ethanol → Benzeneacetic acid, alpha-bromo-, methyl ester

HRID 1743182Notes

Reaction equation

HRID 1743182 reaction equation
S(=O)(=O)(O)O.[Br:6][CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9].[CH2:17](O)C>>[Br:6][CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([O:10][CH3:17])=[O:9]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 97919Bromo(phenyl)acetic acid

Product 1

HCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterYield 79%

Procedure

Concentrated sulfuric acid (0.5 mL) was added to a solution of α-bromophenylacetic acid (3.00 g, 13.9 mmol) in ethanol (30 mL) at room temperature, and the mixture was heated under reflux for 1 hour. The reaction mixture was cooled, and extracted twice with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium hydrogencarbonate, then dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (2.50 g, yield 79%). This was oily.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted twice with ethyl acetate
  5. washwashed with an aqueous saturated sodium hydrogencarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64cad16dbbcb4f66b6ed1c28f9d06c29
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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