Ethanol → Ethyl 2-(4-bromophenyl)acetate

HRID 1428789Notes

Reaction equation

HRID 1428789 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:17][CH3:18])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

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

Product 1

HCID 7020609Ethyl 2-(4-bromophenyl)acetateYield 91%

Procedure

To a stirred solution of 2-(4-bromophenyl)acetic acid (2 g, 9.3 mmol) in ethanol (10 mL) were added sulfuric acid (0.3 mL). The reaction mixture was refluxed for overnight and cooled to room temperature. The solvent was evaporated. The residue was dissolved with ethylacetate and neutralized with NaHCO3. The organic layer was washed with water two times, then dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. ethyl 2-(4-bromophenyl)acetate (2.1 g) was obtained as 91% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved with ethylacetate and neutralized with NaHCO3
  4. washThe organic layer was washed with water two times
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate removed in vacuo
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-88160a247ca049dd970fa1f6010d405c
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

Loading…