Ethanol → Ethyl 3-bromo-4-methoxyphenylacetate

HRID 389258Notes

Reaction equation

HRID 389258 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][CH2:19]O>>[CH2:18]([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)[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1366153-Bromo-4-methoxyphenylacetic acid

Product 1

HCID 57419861Ethyl 3-bromo-4-methoxyphenylacetate

Procedure

To 3-bromo-4-methoxyphenylacetic acid (24 g, 97.9 mmol) in EtOH (240 mL) was added thionyl chloride (7.8 mL, 107.7 mmol), and the reaction was stirred for 35 minutes. Once no starting material was seen by analytical LCMS, the mixture was quenched with NaHCO3 until the solution was basic, and then extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customthe mixture was quenched with NaHCO3 until the solution
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-237a735f99ca456ab170ecb41887a814
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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