Phosphorus oxychloride → 7-Chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridine

HRID 843659Notes

Reaction equation

HRID 843659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[CH:14]=[CH:15][S:16][C:11]3=[C:10](O)[CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:13]=[C:12]2[CH:14]=[CH:15][S:16][C:11]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515622HCID 178515622, compound

Product 1

HCID 154874327-Chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridineYield 88%

Procedure

A solution of 5-(4-fluorophenyl)-thieno[3,2-b]pyridin-7-ol (1.6 g) in phosphorus oxychloride (50 mL) is refluxed for 3 hours. After the excess amount of phosphorus oxychloride is removed under vacuum, the residue is treated with ethyl acetate (20 mL), and NaOH (2N, 20 mL). The mixture is extracted with ethyl acetate (3×20 mL). The combined organic layers are washed with brine and dried over MgSO4. Evaporation of the solvent affords 7-chloro-5-(4-fluorophenyl) thieno[3,2-b]pyridine (1.5 g, 88% yield) as a white solid, m.p. 119-121° C.

Workup

  1. customAfter the excess amount of phosphorus oxychloride is removed under vacuum
  2. additionthe residue is treated with ethyl acetate (20 mL), and NaOH (2N, 20 mL)
  3. extractionThe mixture is extracted with ethyl acetate (3×20 mL)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d7f57d101d0c42079d45ae4ff8eb1793
Source dataset
uspto-grants-2002_04
Patent number
US06380209B1

Reaction notes

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