Iodine → HCID 58566704, compound

HRID 2069686Notes

Reaction equation

HRID 2069686 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[O:3]1.[I:17]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:17][C:8]1[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]2[O:3][C:2]([CH3:16])([CH3:1])[CH2:6][C:5]=2[CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 58566309HCID 58566309, compound

Product 1

HCID 58566704HCID 58566704, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (2.03 g, 9.22 mmol) in methanol (40 mL) was added iodine (2.57 g, 10.14 mmol) and silver sulfate (3.45 g, 11.06 mmol). The reaction was stirred for 3 hours at room temperature and was filtered through celite to remove the solids formed. The solvent was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide ethyl 5-iodo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (829) (3.12 g, 98%) as a red solid.

Workup

  1. filtrationwas filtered through celite
  2. customto remove the solids
  3. customformed
  4. concentrationThe solvent was concentrated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe organic layer was washed with saturated sodium bicarbonate, water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6ffc846c82c41bc9aa68360e2ccd854
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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