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

HRID 1836023Notes

Reaction equation

HRID 1836023 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([F: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>[F:1][C:2]1[CH:3]=[C:4]([F: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 102860365,7-Difluoro-2-(4-methoxy-phenyl)-benzofuran

Product 1

HCID 102145884-(5,7-Difluoro-benzofuran-2-yl)-phenolYield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

Compound 86 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, and the product was purified by column chromatography (eluent 25% EtOAc/hex) to give a solid (0.12 g, 13%): Mp=152-154° C.; 1H NMR (DMSO-d6) δ 10.01 (br s, 1 H), 7.77 (d, 2 H, J=8.9 Hz), 7.32-7.25 (m, 3 H), 6.91 (d, 2 H, J=8.9 Hz); MS 245 [M−H]−

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customdried
  4. customthe product was purified by column chromatography (eluent 25% EtOAc/hex)

Sources & evidence

ORD record
ord-3ed4c88536514143bf1aebe333be2e56
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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