Methanol → Methyl 2-(3-bromo-4-methoxyphenyl)acetate

HRID 456191

Reaction equation

HRID 456191 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:12][C:11](=[O:13])[CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1366153-Bromo-4-methoxyphenylacetic acid

Product 1

HCID 12717575Methyl 2-(3-bromo-4-methoxyphenyl)acetate

Procedure

To 3-bromo-4-methoxyphenylacetic acid (5.226 g, 21.3 mmol) in MeOH (52 mL) was added thionyl chloride (3.1 mL, 42.6 mmol), and the reaction was stirred at room temperature for 2 hours. Once no starting material was seen by analytical LCMS, the mixture was concentrated and the residue was partitioned between CH2Cl2 and 1N aqueous NaOH. The aqueous layer was separated and extracted with CH2Cl2, and the combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 and 1N aqueous NaOH
  3. customThe aqueous layer was separated
  4. extractionextracted with CH2Cl2
  5. washthe combined organic layers were washed with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f37fe2daea384b368ebc4e844e750c25
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Linked notes

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