Ethanol → HCID 117599933, compound

HRID 513238Notes

Reaction equation

HRID 513238 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[CH3:12].OS(O)(=O)=O.[CH3:18][CH2:19]O>>[CH2:18]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([CH3:12])[C:4]=1[I:11])[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14885553HCID 14885553, compound

Product 1

HCID 117599933HCID 117599933, compound

Procedure

A mixture of 4-Bromo-2-iodo-3-methyl-benzoic acid (5.43 g, 0.016 mol) and conc.H2SO4 (5 mL) in EtOH (50 mL) is refluxed overnight. After reaction, evaporated out EtOH, extracted with ethyl acetate (3×50 mL), The combined organic phase is washed with water and brine, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography on silica gel eluted with petrol ether and ethyl acetate to afford the desired compound. Yield: 5.2 g (88%)

Workup

  1. customAfter reaction
  2. customevaporated out EtOH
  3. extractionextracted with ethyl acetate (3×50 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 petrol ether and ethyl acetate

Sources & evidence

ORD record
ord-fd4d38ac70584abd84907a3d1e04b4cd
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

Loading…