3-Bromo-4-fluorobenzaldehyde → HCID 135532429, compound

HRID 650516Notes

Reaction equation

HRID 650516 reaction equation
[S:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[NH2:19][C:20]1[CH:24]=[CH:23][NH:22][N:21]=1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[N:21]3[N:22]=[CH:23][CH:24]=[C:20]3[NH:19][C:5]3[CH2:6][S:1][CH2:2][C:3](=[O:8])[C:4]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 3252862H-Thiopyran-3,5(4H,6H)-dioneHCID 178418806HCID 178418806, compound

Product 1

HCID 135532429HCID 135532429, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,5-thiopyrandione (0.13 g, 1 mmol), 3-bromo-4-fluorobenzaldehyde(0.203 g, 1 mmol), and 3-aminopyrazole (0.082 g, 1 mmol) in ethanol (2 mL) was heated at reflux for 24 hours. After the reaction mixture was allowed to cool to ambient temperature, the volatiles were evaporated at reduced pressure and the resulting residue was chromatographed on silica gel, eluting with 5% ethanol/methylene chloride to provide 0.045 g (12%) of the title compound.

Workup

  1. temperatureat reflux for 24 hours
  2. customthe volatiles were evaporated at reduced pressure
  3. customthe resulting residue was chromatographed on silica gel
  4. washeluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record
ord-93d26c69899d4e33844c59faacac93e5
Source dataset
uspto-grants-2001_08
Patent number
US06274587B1

Reaction notes

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