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

HRID 1862358Notes

Reaction equation

HRID 1862358 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) prepared as described in (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244), 3-bromo-4-fluorobenzaldehyde (0.203 g, 1 mmol), and 3-aminopyrazole (0.082 g, 1 mmol) in ethanol (2 mL) were 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-fc71d0623c9742dea1a7399a813c5136
Source dataset
uspto-grants-2003_03
Patent number
US06538000B1

Reaction notes

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