Ethanol → Ethyl 3-bromo-4-methoxyphenylacetate

HRID 1625670Notes

Reaction equation

HRID 1625670 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 sodium bicarbonate (aqueous) was added until the reaction was of basic pH. 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-cb03510f8df548f2841e2bee175e63ce
Source dataset
uspto-grants-2014_07
Patent number
US08785393B2

Reaction notes

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