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

HRID 1276606Notes

Reaction equation

HRID 1276606 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 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) and the combined organic layers are washed with brine and dried over MgSO4. Evaporation of the solvent gives 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 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-dd01168917ae4d84af34782ea2c702e6
Source dataset
uspto-grants-2000_12
Patent number
US06166203

Reaction notes

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