Iodine → HCID 67057745, compound

HRID 604637Notes

Reaction equation

HRID 604637 reaction equation
[I:1]I.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8]2>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:13]1[CH:12]=[C:11]2[C:7](=[CH:6][C:5]=1[O:4][CH3:3])[CH2:8][CH2:9][CH2:10]2

Participants

5

Reactant 2

HCID 807IodineHCID 2281255-Methoxyindan

Product 1

HCID 67057745HCID 67057745, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of silver sulfate (2.10 g; 6.75 mmol) and iodine (1.71 g; 6.75 mmol) in methanol (20 mL) was treated dropwise over 10 min with a solution of 5-methoxyindane (1 g; 6.75 mmol) in methanol (5 mL). The resultant suspension was stirred at room temperature for 3 h. The reaction was filtered and concentrated in vacuo, slurried with EtOAc (20 mL), and filtered again. The filtrate was concentrated and the residue was purified by flash silica gel chromatography (0-15% EtOAc/hexanes gradient) to afford 5-iodo-6-methoxyindane as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.63 (s, 1H), 6.78 (s, 1H), 3.87 (s, 3H), 2.91-2.85 (m, 4H), 2.15-2.06 (m, 2H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered again
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash silica gel chromatography (0-15% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-3a34edf27859495bbe4827c093420ef4
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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