Iodine → HCID 67518333, compound

HRID 1508466Notes

Reaction equation

HRID 1508466 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1.[I:20]I>C(O)C.C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:20][C:4]1[CH:5]=[C:6]([CH2:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 2

HCID 807IodineHCID 67512835HCID 67512835, compound

Product 1

HCID 67518333HCID 67518333, compound

Reagents, catalysts & solvents 3

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 3-(4-methoxyphenyl)-2,2-dimethylpropanoate (1.45 g, 5.48 mmol) was dissolved in ethanol (55 mL). Iodine (1.392 g, 5.48 mmol) and silver sulfate (1.710 g, 5.48 mmol) were added, and the reaction was stirred vigorously at room temperature, protected from light, for 1 hr. The reaction was 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 tert-butyl 3-(3-iodo-4-methoxyphenyl)-2,2-dimethylpropanoate. 1H NMR (CDCl3, 500 MHz) δ 7.58 (d, J=1.8 Hz, 1H), 7.08 (dd, J=8.4, 1.9 Hz, 1H), 6.71 (d, J=8.4 Hz, 1H), 3.85 (s, 3H), 2.71 (s, 2H), 1.44 (s, 9H), 1.11 (s, 6H).

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-a15c96dc10bf4e11b5fc366a507aae48
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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