Hydrochloric Acid → Ethyl 3-(bromophenyl)acetate

HRID 216216Notes

Reaction equation

HRID 216216 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-3ff37ecbdf284611b966ae6c2176dfa9
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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