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

HRID 1919921Notes

Reaction equation

HRID 1919921 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-methoxy-phenyl)-acetic acid (5.226 g, 21.32 mmol) in MeOH (52 mL) was added thionyl chloride (3.1 mL, 42.65 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 then diluted with CH2Cl2 and aqueous 1N 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. additiondiluted with CH2Cl2 and aqueous 1N 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-c7131f41d0d246be8cc7eca5bd7cae89
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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