5-Bromo-2-(4-methoxyphenyl)benzofuran → 4-(5-Bromo-benzofuran-2-yl)-phenol

HRID 1794515Notes

Reaction equation

HRID 1794515 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][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]=[CH:4][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 101495715-Bromo-2-(4-methoxyphenyl)benzofuranHCID 10176127Pyridinium chloride

Product 1

HCID 102862144-(5-Bromo-benzofuran-2-yl)-phenolYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 81 (0.3 g, 1 mmol) and Pyridine HCl (5 g) was heated to 200° C. After 1 hr, the reaction was cooled and then diluted with water. The aqueous layer was extracted with EtOAc, dried over MgSO4 and concentrated to give a solid. The solid was triturated with CH2Cl2 and filtered to give a solid (0.11 g, 39%); Mp=228–229° C.; 1H NMR (DMSO-d6) δ 9.95 (br s, 1 H), 7.79 (d, 1 H, J=2.0 Hz), 7.74 (d, 2 H, J=8.8 Hz), 7.55 (d, 1 H, J=8.8 Hz), 7.39 (dd, 1 H, J=8.8 Hz, 2.4 Hz), 7.16 (s, 1 H), 6.88 (d, 2 H, J=8.8 Hz); MS 287/289[M−H]−

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe solid was triturated with CH2Cl2
  7. filtrationfiltered

Sources & evidence

ORD record
ord-901ef4e1e8d84d2da38b111ad0f42c75
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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