Imidazole → HCID 69216431, compound

HRID 272727Notes

Reaction equation

HRID 272727 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([O:9][CH3:10])[CH:3]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 160792304-Chloro-1-iodo-2-methoxybenzene

Product 1

HCID 69216431HCID 69216431, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-chloro-1-iodo-2-methoxy-benzene (0.268 g, 1 mmol), imidazole (0.082 g, 1.2 mmol), 1,0-phenanthroline (0.018 g, 0.1 mmol), CuI (0.01 g, 0.05 mmol), and Cs2CO3 (0.684 g, 2.1 mmol) in dioxane (1.5 mL) was heated at 110° C. for 24 hours. After the reaction mixture cooled to room temperature, it was partitioned between H2O and EtOAc. The aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with EtOAc to give 0.095 g of the title compound (46%). MS (APCI) m/e 209 (M+H)+, 1H NMR (500 MHz, DMSO-d6): □ 7.44 (s, 1H), 7.43 (s, 1H), 7.35 (d, J=2.14 Hz, 2H), 7.15 (d, J=2.14 Hz, 1H), 7.13 (d, J=2.14 Hz, 1H), 3.86 (s, 3H).

Workup

  1. temperatureAfter the reaction mixture cooled to room temperature
  2. customit was partitioned between H2O and EtOAc
  3. extractionThe aqueous layer was extracted with additional EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with EtOAc

Sources & evidence

ORD record
ord-9ebd2d37f48848a48dc298c389bb17f1
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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