Ethanol → Ethyl 2-(4-bromophenyl)acetate

HRID 1207

Reaction equation

HRID 1207 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.OS(O)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH2:23](O)[CH3:24]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:23][CH3:24])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 7020609Ethyl 2-(4-bromophenyl)acetate

Procedure

A solution of 43 g (200 mmol) of 4-bromophenylacetic acid and 0.2 g of conc. H2SO4 in 470 ml of ethanol was refluxed for 16 hours. The reaction mixture was cooled to ambient temperature, stirred with 6 g of solid K2CO3 for 30 minutes and then filtered. The filtrate was concentrated in vacuo, diluted with Et2O (200 ml), washed with 10% aqueous NaHCO3 (10 ml) and brine (10 ml), dried over MgSO4 and concentrated in vacuo to give the title compound as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additiondiluted with Et2O (200 ml)
  4. washwashed with 10% aqueous NaHCO3 (10 ml) and brine (10 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c9f9ed9d7a3470fad54d7ea759b23b8
Source dataset
uspto-grants-1998_03
Patent number
US05723620

Linked notes

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