Cesium carbonate → HCID 69205339, compound

HRID 2118097Notes

Reaction equation

HRID 2118097 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7](O)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH3:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1I.Cl.CN(C)CC(O)=[O:28].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.CN(C=O)C.[Cu](I)I>[CH3:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[O:28][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 1288446-HydroxybenzofuranHCID 210779091-Iodo-2-methyl-4-(trifluoromethyl)benzene

Product 1

HCID 69205339HCID 69205339, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 1-benzofuran-6-ol (309 mg, 2.3 mmol) in dioxane (6 mL) and DMF (12 mL) was added 2-methyl-4-trifluoromethylphenyl iodide (600 mg, 2.3 mmol), copper iodide (108 mg, 0.57 mmol), dimethylglycine hydrochloride (243 mg, 1.7 mmol), and cesium carbonate (1.88 g, 5.8 mmol). The reaction was stirred at 110° C. for 22 h. After cooling to room temperature, solvents were removed in vacuo. The residue was dissolved in ethyl acetate, washed with water and brine, dried and concentrated. The crude product was purified on a silica gel column, eluting with ethyl acetate (0-10%) in hexanes. The final product was collected as a slightly yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customsolvents were removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified on a silica gel column
  8. washeluting with ethyl acetate (0-10%) in hexanes
  9. customThe final product was collected as a slightly yellow oil

Sources & evidence

ORD record
ord-39cc35e2e9c9463ebdfd5d14a4f53d73
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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