Phosphorus oxychloride → 4-Chloro-6-(4-bromophenyl)thieno[3,2-c]pyridine

HRID 1006940Notes

Reaction equation

HRID 1006940 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]3[CH:15]=[CH:16][S:17][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:12]1[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 225024536-(4-bromophenyl)-5H-thieno[3,2-c]pyridin-4-one

Product 1

HCID 225035574-Chloro-6-(4-bromophenyl)thieno[3,2-c]pyridine

Conditions

Temperature
100 °C

Procedure

6-(4-Bromophenyl)-5H-thieno[3,2-c]pyridin-4-one (4.87 g) was added to phosphorus oxychloride (30 ml), and the resulting mixture was heated at 100° C. for 3 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and water. The organic layer was washed with water, an aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, to give 4-chloro-6-(4-bromophenyl)thieno[3,2-c]pyridine.

Workup

  1. customThe reaction solution was evaporated
  2. additionto the resulting residue were added ethyl acetate and water
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-175c5a0656fd485a9a7f78511c200b2c
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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