Potassium Carbonate → 6-[(3-Iodobenzyl)oxy]-1-benzofuran

HRID 2118101Notes

Reaction equation

HRID 2118101 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[I:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[I:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][O:10][C:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1288446-HydroxybenzofuranHCID 27593613-Iodobenzyl bromide

Product 1

HCID 590100686-[(3-Iodobenzyl)oxy]-1-benzofuran

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-benzofuran-6-ol (1.0 g, 7.5 mmol) and 3-iodobenzylbromide (2.7 g, 9.0 mmol) in DMF (10 mL) was added potassium carbonate (1.5 g, 11.0 mmol). The reaction mixture was stirred under nitrogen at room temperature for 3 days. The reaction was diluted with ethyl acetate, washed with water (2×) and brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified on a silica gel column, eluting with ethyl acetate (10-50%) in hexane. The final product was collected as a slightly yellow viscous oil.

Workup

  1. washwashed with water (2×) and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column
  6. washeluting with ethyl acetate (10-50%) in hexane
  7. customThe final product was collected as a slightly yellow viscous oil

Sources & evidence

ORD record
ord-94363deccc2647bcb8c3d32f1841093c
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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