Pyridinium chloride → Phenol, 4-(5-chloro-2-benzofuranyl)-

HRID 1794516Notes

Reaction equation

HRID 1794516 reaction equation
[Cl: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>[Cl: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 10176127Pyridinium chlorideHCID 102362405-Chloro-2-(4-methoxyphenyl)benzofuran

Product 1

HCID 10171444Phenol, 4-(5-chloro-2-benzofuranyl)-Yield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 82 (0.5 g, 1.9 mmol) and Pyridine HCl (10 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 (0.20 g, 47%); Mp=216–218° C.; 1H NMR (DMSO-d6) δ 9.95 (br s, 1 H), 7.74 (d, 2 H, J=8.8 Hz),7.66 (d, 1 H, J=1.9 Hz), 7.59 (d, 1 H, J=8.8 Hz), 7.27 (dd, 1 H, J=8.8 Hz, 2.4 Hz), 7.17 (s, 1 H), 6.88 (d, 2 H, J=8.7 Hz); MS 243/245 [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-c86a7724efee4276bf035ab057ce0501
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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