Phenol → 5-Iodo-2-phenoxymethyl-benzofuran

HRID 1171219Notes

Reaction equation

HRID 1171219 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:6]=2[CH:7]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[Na+].[Cl-]>CN(C)C=O>[I:12][C:9]1[CH:10]=[CH:11][C:5]2[O:4][C:3]([CH2:2][O:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:6]=2[CH:8]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 687159772-Bromomethyl-5-iodo-benzofuran

Product 1

HCID 576082155-Iodo-2-phenoxymethyl-benzofuranYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide (20 mL) solution of 2-bromomethyl-5-iodo-benzofuran (270 mg, 0.801 mmol) and phenol (113 mg, 1.2 mmol) was added potassium carbonate (332 mg, 2.4 mmol). This mixture was stirred at room temperature for 14 hours. The reaction mixture was poured into sat. NaCl and extracted with ethyl acetate. The organic layer was separated and dried over anhydrous magnesium sulfate followed by concentrating under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to obtain the title compound (251 mg, 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationby concentrating under a reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-3e1d09166ac24f42aff404b2d76df760
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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