Iodine → Ethyl 3-(2-fluoro-5-iodo-4-methoxyphenyl)propanoate

HRID 1508468Notes

Reaction equation

HRID 1508468 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[I:17]I>C(O)C.C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Ag+2]>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:17])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 2

HCID 807IodineHCID 23083097Ethyl 3-(2-Fluoro-4-methoxyphenyl)propanoate

Product 1

HCID 67513537Ethyl 3-(2-fluoro-5-iodo-4-methoxyphenyl)propanoate

Reagents, catalysts & solvents 3

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-(2-fluoro-4-methoxyphenyl)propanoate (1480 mg, 6.54 mmol) was dissolved in ethanol (60 mL). Iodine (1660 mg, 6.54 mmol) and silver sulfate (2040 mg, 6.54 mmol) were added and the reaction was stirred vigorously at room temperature, protected from light, for 1 hr. The reaction was then diluted with ethyl acetate (100 mL) and filtered. The filtrate was washed with sodium bisulfite (2×60 mL), water (70 mL), and brine (70 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel with 0 to 50% ethyl acetate/hexanes to afford ethyl 3-(2-fluoro-5-iodo-4-methoxyphenyl)propanoate. 1H NMR (CDCl3, 500 MHz) δ 7.59 (d, J=8.4 Hz, 1H), 6.55 (d, J=11.6 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 3.84 (s, 3H), 2.87 (t, J=7.6 Hz, 2H), 2.57 (t, J=7.6 Hz, 2H), 1.24 (t, J=7.1 Hz, 3H).

Workup

  1. customfor 1 hr
  2. filtrationfiltered
  3. washThe filtrate was washed with sodium bisulfite (2×60 mL), water (70 mL), and brine (70 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel with 0 to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7377c09e11fb44acb6c1abccc32d215d
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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