Ethanol → HCID 91882220, compound

HRID 513222Notes

Reaction equation

HRID 513222 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([I:11])[CH:3]=1.[CH2:12](O)[CH3:13]>S(Cl)(Cl)=O>[CH2:12]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[I:11])[CH3:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 190915044-Bromo-2-iodobenzoic acid

Product 1

HCID 91882220HCID 91882220, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-2-iodo-benzoic acid (4.0 g; 12.24 mmol) is stirred in thionyl chloride (8.0 ml) under reflux for 1 hour. The reaction mixture is evaporated under reduced pressure and taken up immediately in 20 ml methylene dichloride and cooled down to 0° C. Ethanol (20.0 ml; 342.96 mmol) is added and stirred for 1 hour at ambient temperature. The ethanol is evaporated and the residue taken up in methylene dichloride and extracted with saturated NaHCO3 solution. The organic layer is separated, dried over MgSO4 and evaporated to dryness.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customThe ethanol is evaporated
  4. extractionextracted with saturated NaHCO3 solution
  5. customThe organic layer is separated
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-17cdf5ccef394070bdbbe23256e05bb4
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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