Sulfuric Acid → Methyl 2-(2-bromophenyl)acetate

HRID 1866806Notes

Reaction equation

HRID 1866806 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([OH:16])=[O:15].[C:17]([O-])(O)=O.[Na+]>CO>[CH3:17][O:15][C:14](=[O:16])[CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[Br:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 877542-Bromophenylacetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 8063364Methyl 2-(2-bromophenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 mL H2SO4 is added to (2-bromo-phenyl)-acetic acid (15 g, 70 mmol) in 150 mL methanol. The reaction mixture is refluxed 16 hours and cooled to room temperature. 100 mL saturated NaHCO3 (aq) is added. Methanol is removed in vacuo. The resulting mixture is extracted with Ethyl acetate. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give the title compound.

Workup

  1. temperatureThe reaction mixture is refluxed 16 hours
  2. customMethanol is removed in vacuo
  3. extractionThe resulting mixture is extracted with Ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb6679c6396d48a0a5d6f49d1cb8e529
Source dataset
uspto-grants-2009_12
Patent number
US07629473B2

Reaction notes

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