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

HRID 1276602Notes

Reaction equation

HRID 1276602 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 then 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 then 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-857dc65571a24ac4be51ee1cae8d8a59
Source dataset
uspto-grants-2000_12
Patent number
US06166203

Reaction notes

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