Ethanol → Ethyl 3-bromo-4-methoxyphenylacetate

HRID 1625662Notes

Reaction equation

HRID 1625662 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-methoxy-phenyl)-acetic acid (24 g, 97.9 mmol) in ethanol (240 mL) was added thionyl chloride (78 mL, 107.7 mmol) and the reaction was stirred at room temperature for 1.5 hours. Once no starting material was seen by analytical LCMS, saturated NaHCO3 (aq.) was added until the reaction was basic. The mixture was extracted twice with dichloromethane and the combined organic layers were washed with water, dried over magnesium sulfate, filtered, and concentrated to give the title compound.

Workup

  1. additionwas added until the reaction
  2. extractionThe mixture was extracted twice with dichloromethane
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7cea5d7fee084ea690baa9b97cba2482
Source dataset
uspto-grants-2014_07
Patent number
US08785393B2

Reaction notes

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