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

HRID 1871587Notes

Reaction equation

HRID 1871587 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 combinded 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 combinded organic layers are washed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-08bef148215f4c0e84ff78b8e1797e49
Source dataset
uspto-grants-2000_08
Patent number
US06103903

Reaction notes

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