Ethyl Acetate → HCID 929387, compound

HRID 1197997Notes

Reaction equation

HRID 1197997 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.C1C(=O)N([I:19])C(=O)C1.C(OCC)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[C:4]([I:19])[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 94475-Chlorosalicylic AcidHCID 120273N-Iodosuccinimide

Product 1

HCID 929387HCID 929387, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5-Chlorosalicylic acid (20 g, 115.8 mmol) is dissolved in DMF (100 mL). To this solution is added NIS (26.1 g, 116.0 mmol) which causes the reaction to warm up to 60° C. The reaction is stirred at room temperature for 20 hours. At this point ethyl acetate (100 mL) is added and the solution washed with 0.1N HCl (100 mL). The organic phase is then washed with water (3×100 mL), dried with sodium sulfate and evaporated under reduced pressure to yield 5-chloro-3-iodosalicylic acid as off-white solid. (mp 160°-163° C.)

Workup

  1. customthe reaction
  2. washthe solution washed with 0.1N HCl (100 mL)
  3. washThe organic phase is then washed with water (3×100 mL)
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-be2416c55ade49ada6bc303c015b3508
Source dataset
uspto-grants-1994_01
Patent number
US05278323

Reaction notes

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