Methyl 4-iodobenzoate → HCID 10236364, compound

HRID 1836045Notes

Reaction equation

HRID 1836045 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](B(O)O)=[CH:8][C:7]=2[CH:14]=1.I[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.CCO>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]=3[CH:8]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 69273Methyl 4-iodobenzoateHCID 22221596(5-Methoxy-1-benzofuran-2-yl)boronic acid

Product 1

HCID 10236364HCID 10236364, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 5-Methoxy-benzofuran-2-boronic acid (1.9 g, 10 mmol), Methyl 4-iodobenzoate (2.61 g, 10 mmol), Pd(Ph3)4 (0.25 g), and 2M NaCO3 (10 ml) in toluene (40 ml) and EtOH (10 ml) was heated to reflux. After 2 hr, the reaction was cooled and the organic layer was seperated dried, and concentrated to give a solid. The solid was triturated with MeOH, filtered to give 127 (0.90 g, 32%) which was used without further purification or characterization for the next step.

Workup

  1. temperaturethe reaction was cooled
  2. customthe organic layer was seperated
  3. customdried
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe solid was triturated with MeOH
  7. filtrationfiltered

Sources & evidence

ORD record
ord-439c105a8a844ce5a531f1d4e9c782c0
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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