Phosphorus oxychloride → 7-Chlorothieno[3,2-b]pyridine

HRID 1972173Notes

Reaction equation

HRID 1972173 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2O)[CH:3]=[CH:2]1.O=P(Cl)(Cl)[Cl:13]>ClC(Cl)C>[Cl:13][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[CH:2][S:1][C:9]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

HCID 112752517-Chlorothieno[3,2-b]pyridineYield 74.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of thieno[3,2-b]pyridin-7-ol (2.50 g, 16.5 mmol) and POCl3 (3.1 mL, 33 mmol) in dichloroethane (10 mL) was stirred for 2 hours at reflux. The mixture was concentrated and the dark residue was resuspended in dichloromethane (50 mL). The solution was carefully neutralized with saturated NaHCO3 solution. The mixture was extracted with dichloromethane, dried over MgSO4, and concentrated to give the title compound (2.09 g, 74%) as a brown solid.

Workup

  1. temperatureat reflux
  2. concentrationThe mixture was concentrated
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e76c472cde74f8d8b34ac63923449ac
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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