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

HRID 734309Notes

Reaction equation

HRID 734309 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.O=P(Cl)(Cl)[Cl:14]>>[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)pyridine

Procedure

3-Bromo-5H-thieno[3,2-c]pyridin-4-one (1.0 g) and POCl3 (3 ml) was stirred for 1.5 hours at 120° C. After evaporation of POCl3, crushed ice was added to the residue and generated precipitate was collected by filtration to afford 3-bromo-4-chloro-thieno[3,2-c]pyridine (1.1 g) 1H NMR (400 MHz, DMSO-d6) ppm 8.31 (d, J=5.6 Hz, 1H), 5.27-8.21 (m, 2H).

Workup

  1. customAfter evaporation of POCl3
  2. customcrushed ice
  3. additionwas added to the residue
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-816de89bc8694e4e8d4bb8bd99ae5494
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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