Ethanol → HCID 117599790, compound

HRID 513234Notes

Reaction equation

HRID 513234 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([I:11])[C:3]=1[O:12][CH3:13].OS(O)(=O)=O.[CH3:19][CH2:20]O>>[CH2:19]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([O:12][CH3:13])[C:4]=1[I:11])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 117599765HCID 117599765, compound

Product 1

HCID 117599790HCID 117599790, compound

Procedure

A mixture of 4-Bromo-2-iodo-3-methoxy-benzoic acid (12.0 g, 0.0336 mol) and conc.H2SO4 (20 mL) in EtOH (200 mL) is refluxed overnight. After reaction, evaporated out EtOH and the mixture is extracted with ethyl acetate (3×1000 mL). The combined organic phase is washed with water and brine, dried over Na2SO4, concentrated in vacuo, purified by column chromatography on silica gel eluted with petroleum ether/ethyl acetate=20:1 to afford the desired product as a colourless oil.

Workup

  1. customAfter reaction
  2. customevaporated out EtOH
  3. extractionthe mixture is extracted with ethyl acetate (3×1000 mL)
  4. washThe combined organic phase is washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography on silica gel
  8. washeluted with petroleum ether/ethyl acetate=20:1

Sources & evidence

ORD record
ord-fa4fe8b8d67d4189ba8aaef0dc1b75be
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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