Phosphorus oxychloride → 3-Bromo-4-chlorothieno(3,2-c)pyridine

HRID 1505630Notes

Reaction equation

HRID 1505630 reaction equation
[Br:1][C:2]1[C:6]2[C:7](=O)[NH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.P(Cl)(Cl)([Cl:14])=O>>[Br:1][C:2]1[C:6]2[C:7]([Cl:14])=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 184507963-Bromothieno[3,2-c]pyridin-4(5H)-one

Product 1

HCID 184507733-Bromo-4-chlorothieno(3,2-c)pyridineYield 32%

Procedure

A stirred mixture of 3-bromo-5H-thieno[3,2-c]pyridine-4-one (1.16 g, 5.04 mmol) and phosphorus oxychloride (20 ml) was heated to reflux for 4 h. The reaction was then allowed to cool to room temperature and the phosphorus oxychloride removed in vacuo. The residue was dissolved in DCM (25 ml) and washed with distilled water (2×25 ml) followed by saturated sodium hydrogen carbonate solution (25 ml). The organic layer was dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was then subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 5:1, Rf 0.5) to afford the title compound as a yellow solid (398 mg, 32%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customthe phosphorus oxychloride removed in vacuo
  4. dissolutionThe residue was dissolved in DCM (25 ml)
  5. washwashed with distilled water (2×25 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customwas then subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 5:1, Rf 0.5)

Sources & evidence

ORD record
ord-54714dc95ca6413fa8c972e4723cb5f3
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

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