Pyridinium chloride → 4-(5,7-Dibromo-benzofuran-2-yl)-phenol

HRID 1836024Notes

Reaction equation

HRID 1836024 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Br:19])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:18]=1.Cl.N1C=CC=CC=1>O>[Br:1][C:2]1[CH:3]=[C:4]([Br:19])[C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)=[CH:7][C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 103094045,7-Dibromo-2-(4-methoxy-phenyl)benzofuran

Product 1

HCID 103091974-(5,7-Dibromo-benzofuran-2-yl)-phenolYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

Compound 87 was treated with Pyridine HCl (5 g) and heated to 200° C. After 1 hr, the reaction was cooled and diluted with water. The aqueous layer was extracted with EtOAc, dried over MgSO4, and the product was purified by column chromatography (eluant 25% EtOAc/hexanes) to give a solid (0.12 g, 18%); Mp=203-205° C.; 1H NMR (DMSO-d6) δ 10.04 (br s, 1 H), 7.83 (d, 1 H, J=1.5 Hz), 7.75 (d, 2 H, J=8.3 Hz), 7.68 (d, 1 H, J=2.0 Hz), 7.28 (s, 1 H), 6.91 (d, 2 H, J=8.3 Hz); MS 365/367/369 [M−H]−

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customthe product was purified by column chromatography (eluant 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fb9863b2285c4ac8973ea9ac96d72cd2
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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