Ethanol → Ethyl 3-bromo-4-methoxyphenylacetate

HRID 553659Notes

Reaction equation

HRID 553659 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.C([O-])(O)=O.[Na+].[CH2:23](O)[CH3:24]>>[CH2:23]([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)[CH3:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1366153-Bromo-4-methoxyphenylacetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 57419861Ethyl 3-bromo-4-methoxyphenylacetate

Procedure

To 3-bromo-4-methoxyphenylacetic acid (24 g, 97.9 mmol) in ethanol (240 mL) was added thionyl chloride (7.8 mL, 107.7 mmol), and the reaction was stirred at room temperature for 1 hour. Once no starting material was seen by analytical LCMS, the mixture was basified with saturated aqueous NaHCO3 and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the desired product.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-edc7daea5a054297af3eeba2d3d0a5f3
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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