Hydrochloric Acid → Ethyl 3-(bromophenyl)acetate

HRID 2110744Notes

Reaction equation

HRID 2110744 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:13][CH2:14]O>>[CH2:13]([O:11][C:10](=[O:12])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Br:2])[CH:4]=1)[CH3:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11470552Ethyl 3-(bromophenyl)acetateYield 93.4%

Conditions

Temperature
0 °C

Procedure

HCl is bubbled through a solution of 3-bromophenyl acetic acid (10.5 g, 46.5 mmol) in EtOH (70 mL) chilled at 0° C. for 5 minutes. The flask is capped and stirred at ambient temperature for 5 hours. The mixture is concentrated. The residue is taken up with water (80 mL) and extracted twice with EtOAc (70 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford (3-bromo-phenyl)-acetic acid ethyl ester [10.55 g, 93.4%] as an oil, which is used without further purification.

Workup

  1. customThe flask is capped
  2. concentrationThe mixture is concentrated
  3. extractionextracted twice with EtOAc (70 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-60713a3a94c44a2a8ad3565747bcfc84
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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