4-Iodophenol → HCID 22379572, compound

HRID 895371Notes

Reaction equation

HRID 895371 reaction equation
[I:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=2)=[CH:4][CH:3]=1.IC1C=CC(O)=CC=1.[H][H]>O1CCCC1.[Ni].O>[I:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 108944-IodophenolHCID 22379664HCID 22379664, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22379572HCID 22379572, compoundYield 92.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Iodo-phenoxy)-5-nitro-pyridine (50 grams, 146.1 mmol) and 4-iodo-phenol (96.5 grams, 438.6 mmol) were dissolved in tetrahydrofuran (500 mL) and added to a Parr shaker flask which contained Raney nickel (30 grams of a 50% slurry in water). The above mixture was shaken under hydrogen gas (50 psi) for 2 hours, at which time uptake of hydrogen gas had ceased and thin liquid chromatography indicated complete consumption of starting material. The Raney nickel was then removed by filtration through a pad of celite under nitrogen. The pad was rinsed several times with methylene chloride. The filtrate was diluted with methylene chloride and the organic layer was washed with 1M sodium hydroxide (4×200 mL) and brine (1×200 mL). The organic layer was dried with magnesium sulfate, filtered and concentrated under vacuum to give 42 grams (92%) of the title compound which was used without further purification. MS m/z: ESI+ 313.0 (M+H)+.

Workup

  1. additionadded to a Parr shaker flask which
  2. customconsumption of starting material
  3. customThe Raney nickel was then removed by filtration through a pad of celite under nitrogen
  4. washThe pad was rinsed several times with methylene chloride
  5. additionThe filtrate was diluted with methylene chloride
  6. washthe organic layer was washed with 1M sodium hydroxide (4×200 mL) and brine (1×200 mL)
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-04a91e1f68ab4a448628d1aee9a347f5
Source dataset
uspto-grants-2005_07
Patent number
US06916807B2

Reaction notes

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