Ethanol → Ethyl 3-(bromophenyl)acetate

HRID 1181592Notes

Reaction equation

HRID 1181592 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:17][CH3:18])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11470552Ethyl 3-(bromophenyl)acetate

Procedure

3-Bromophenylacetic acid (5.03 g) was dissolved in ethanol (40 ml), conc. sulfuric acid (0.5 ml) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate and brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (5.4 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-922dbfa059ec465ba410a4cc69d9d900
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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