Iodine → HCID 44419910, compound

HRID 1508459Notes

Reaction equation

HRID 1508459 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[I:14]I>CO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[I:14][C:8]1[CH:7]=[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 807IodineHCID 90266Methyl 4-methoxyphenylacetate

Product 1

HCID 44419910HCID 44419910, compound

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl (4-methoxyphenyl)acetate (1 mL, 6.3 mmol) in MeOH (40 mL) was added Ag2SO4 (1.96 g, 6.3 mmol) followed by I2 (1.6 g, 6.3 mmol). The reaction was stirred vigorously at room temperature for 1 hour and then the solids were removed by filtration. The filtrate was diluted with EtOAc (200 mL), and washed with aq. NaHSO3 (2×50 mL) and brine (2×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford methyl (3-iodo-4-methoxyphenyl)acetate. Rf=0.27 (15% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3) δ 7.68 (d, J=2.0 Hz, 1H), 7.21 (dd, J=8.2, 1.8 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 3.85 (s, 3H), 3.68 (s, 3H), 3.52 (s, 2H).

Workup

  1. customthe solids were removed by filtration
  2. additionThe filtrate was diluted with EtOAc (200 mL)
  3. washwashed with aq. NaHSO3 (2×50 mL) and brine (2×50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed2ff06a00524bcfbd9874c5548882c3
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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