4-Iodophenol → HCID 60645354, compound

HRID 1057163Notes

Reaction equation

HRID 1057163 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[I:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>CN(C=O)C.CCOC(C)=O>[I:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 73277Chloropyrazine

Product 1

HCID 60645354HCID 60645354, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of chloropyrazine (124 mg, 1.08 mmol), K2CO3 (749 mg, 5.42 mmol), and 4-iodophenol (263 mg, 1.20 mmol) in DMF (24 mL) was heated at 100° C. for 9.5 h and then stirred at rt overnight. The reaction was diluted with EtOAc and washed with H2O (40 mL). The aqueous wash was back extracted with EtOAc (20 mL). The organic extracts were combined, washed with H2O (2×40 mL), washed with brine (40 mL), dried (MgSO4), filtered, concentrated and purified by silica gel chromatography (0%-20% EtOAc in hexanes) to give 289 mg of 2-(4-iodophenoxy)pyrazine (containing 15% of 4-iodophenol) as a white semi-solid. 1H NMR (400 MHz, DMSO-d6): δ 8.57 (d, 1H), 8.41 (d, 1H), 8.21 (dd, 1H), 7.78 (d, 2H), 7.07 (d, 2H).

Workup

  1. washwashed with H2O (40 mL)
  2. washThe aqueous wash
  3. extractionwas back extracted with EtOAc (20 mL)
  4. washwashed with H2O (2×40 mL)
  5. washwashed with brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (0%-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e9bed8276fc544e4b53ef93ed5725af8
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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