5,7-Dichloro-2-(4-methoxy-phenyl)-benzofuran → 4-(5,7-Dichloro-benzofuran-2-yl)-phenol

HRID 1836022Notes

Reaction equation

HRID 1836022 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]([Cl: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 101254875,7-Dichloro-2-(4-methoxy-phenyl)-benzofuranHCID 10176127Pyridinium chloride

Product 1

HCID 101493784-(5,7-Dichloro-benzofuran-2-yl)-phenolYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 85 (0.7 g, 2.4 mmol) and Pyridine HCl (10 g) was heated to 200° C. After 1 Hr, the reaction was cooled and diluted with water. The aqueous layer was extracted with EtOAc, dried and concentrated to give a solid which was triturated with MeOH, filtered to give a solid (0.5 g, 75%): Mp=184-186° C.; 1H NMR (DMSO-d6) δ 10.04 (s, 1 H), 7.77 (d, 2 H, J=8.3 Hz), 7.67 (t, 1 H, J=0.8 Hz), 7.48-7.46 (m, 1 H), 7.26 (s, 1 H), 6.90 (d, 2H, J=8.2 Hz); MS 277/279 [M−H]−

Workup

  1. temperatureAfter 1 Hr, the reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with MeOH
  7. filtrationfiltered

Sources & evidence

ORD record
ord-28b116897f034d9c915925c2b16a55ad
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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