Ethanol → Ethyl 2-(4-bromophenyl)acetate

HRID 1373248Notes

Reaction equation

HRID 1373248 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.[CH2:17](O)[CH3:18]>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 7020609Ethyl 2-(4-bromophenyl)acetateYield 99%

Procedure

Concentrated sulfuric acid (10 ml) was added to an ethanol (300 ml) solution of 4-bromophenylacetic acid (25 g, 120 mmols), and heated under reflux for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was poured into water with ice, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure to give an oil of ethyl 4-bromophenylacetate (28 g, 99%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was poured into water with ice
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6089fc3a8f3c4669b5db89127482671c
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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