Iodine → HCID 67513780, compound

HRID 1508462Notes

Reaction equation

HRID 1508462 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.[I:17]I>C(O)C.C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:17][C:8]1[CH:7]=[C:6]([C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 2

HCID 807IodineHCID 67513543HCID 67513543, compound

Product 1

HCID 67513780HCID 67513780, compound

Reagents, catalysts & solvents 3

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-(4-methoxyphenyl)-3-methylbutanoate (475 mg, 2.137 mmol) was dissolved in ethanol (20 mL). Iodine (542 mg, 2.137 mmol) and silver sulfate (666 mg, 2.137 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 (40 mL) and filtered. The filtrate was washed with sodium bisulfite (2×50 mL), water (50 mL), and brine (50 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 methyl 3-(3-iodo-4-methoxyphenyl)-3-methylbutanoate. 1H NMR (CDCl3, 500 MHz) δ 7.73 (d, J=2.5 Hz, 1H), 7.29 (dd, J=8.6, 2.5 Hz, 1H), 6.75 (d, J=8.4 Hz, 1H), 3.86 (s, 3H), 3.55 (s, 3H), 2.57 (s, 2H), 1.41 (s, 6H).

Workup

  1. customfor 1 hr
  2. filtrationfiltered
  3. washThe filtrate was washed with sodium bisulfite (2×50 mL), water (50 mL), and brine (50 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-dc38fe3792fa40508987501bd2e7921e
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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