Potassium Iodide → HCID 67324883, compound

HRID 1616908Notes

Reaction equation

HRID 1616908 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[I:8][C:9]1[CH:10]=[C:11]([O:18]C)[C:12](=[CH:16][CH:17]=1)[C:13]([O-:15])=[O:14].[C:20](=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:18][C:11]1[CH:10]=[C:9]([I:8])[CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH3:20])=[O:14])[CH3:7]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22361522HCID 22361522, compound

Product 1

HCID 67324883HCID 67324883, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl bromoacetate (80 mL; 0.72 mol, Aldrich, 98%) was added to a solution of 4-iodo-methylsalicylate (200 g, 0.72 mol; 1.0 eq), potassium carbonate (198 g, 2 eq, 1.44 mol) and potassium iodide (17.8 g 0.107 mol 0.15 eq) in acetone under nitrogen. The reaction was stirred at 50° C. for 5 h and at r.t. for 16 h. The reaction mixture was filtered and the solid was washed with acetone. The liquors were concentrated to a dark brown oil and dried under house vacuum to afford 241 g of methyl 2-(2-ethoxy-2-oxoethoxy)-4-iodobenzoate. 1H-NMR (400 MHz, CDCl3): δ 1.31 (t, 3H), 3.89 (s, 3H), 4.28 (q, 2H), 4.70 (s, 2H), 7.22 (d, 1H), 7.41 (dd, 1H), 7.54 (d, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with acetone
  3. concentrationThe liquors were concentrated to a dark brown oil
  4. customdried under house vacuum

Sources & evidence

ORD record
ord-0db49450f1ef44e4afd4e76d6f438921
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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