Iodine → HCID 67057719, compound

HRID 537981Notes

Reaction equation

HRID 537981 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])=[CH:5][CH:4]=1.[I:14]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[I:14][C:4]1[CH:5]=[C:6]([C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 807IodineHCID 12830786HCID 12830786, compound2×

Product 1

HCID 67057719HCID 67057719, compound

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(4-methoxyphenyl)-2-methylpropan-1-ol (661.7 mg, 3.68 mmol) (2-(4-methoxyphenyl)-2-methylpropan-1-ol has been described in the literature. See Helv. Chim. Acta. 1971, 54, p. 868-897.) in EtOH (40 mL) was added Ag2SO4 (1.15 g, 3.68 mmol) followed by I2 (934 mg, 3.68 mmol). The reaction was stirred at room temperature for 2 hours, and then the solids were filtered off through a pad of Celite. The filtrate was concentrated to ˜10 mL and then diluted with EtOAc (50 mL). The organic solution was washed with water, aq. NaHSO3, and brine (15 mL each). The organic layer was then diluted with 50 mL of hexanes and filtered through a short plug of silica gel with (50/50 EtOAc/hexanes). The filtrate was concentrated to afford 2-(3-iodo-4-methoxyphenyl)-2-methylpropan-1-ol. 1H NMR (CDCl3, 500 MHz) δ 7.76 (d, J=2.3 Hz, 1H), 7.32 (dd, J=8.7, 2.3 Hz, 1H), 6.79 (d, J=8.7 Hz, 1H), 3.87 (s, 3H), 3.57 (s, 2H), 1.30 (s, 6H).

Workup

  1. filtrationthe solids were filtered off through a pad of Celite
  2. concentrationThe filtrate was concentrated to ˜10 mL
  3. additiondiluted with EtOAc (50 mL)
  4. washThe organic solution was washed with water, aq. NaHSO3, and brine (15 mL each)
  5. additionThe organic layer was then diluted with 50 mL of hexanes
  6. filtrationfiltered through a short plug of silica gel with (50/50 EtOAc/hexanes)
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ee82f8e948ff47548e33d3eae5a07043
Source dataset
uspto-grants-2014_10
Patent number
US08865707B2

Reaction notes

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