Phosphorus oxychloride → 7-Chloro-furo(3,2-b)pyridine

HRID 1192403Notes

Reaction equation

HRID 1192403 reaction equation
[O:1]1[C:9]2[C:4](=[N+:5]([O-])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O=P(Cl)(Cl)[Cl:13]>C(Cl)(Cl)Cl>[Cl:13][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[CH:2][O:1][C:9]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10630536Furo[3,2-b]pyridine 4-oxide

Product 1

HCID 105588227-Chloro-furo(3,2-b)pyridineYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of Furo[3,2-b]pyridine 4-oxide in CHCl3 (5 mL) was added POCl3 (5 g, 33 mmol). The mixture was refluxed for 2 hours. After cooling, the mixture was quenched with ice water and neutralized with NaHCO3. Extracted with CHCl3 (3×100 mL). The organic phase was dried and concentrated. The residue was subject to column chromatography to afford 7-Chloro-furo[3,2-b]pyridine (0.74 g, 50%). 1H NMR (CDCl3, 400 MHz) δ 8.46 (m, 1H), 7.92 (m, 1H), 7.28 (m, 1H), 7.04 (m, 1H).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe mixture was quenched with ice water and neutralized with NaHCO3
  4. extractionExtracted with CHCl3 (3×100 mL)
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-926ffa6789c04083a3c3f9ac460a46c8
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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