Tetrahydrofuran → HCID 18668938, compound

HRID 1058656Notes

Reaction equation

HRID 1058656 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[CH:22]=[CH:23][C:24]([F:29])=[C:25]([CH:28]=1)[CH:26]=[O:27].[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>C([Sn](CCCC)(CCCC)C1OC=CC=1)CCC>[F:29][C:24]1[CH:23]=[CH:22][C:21]([C:31]2[O:30][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:25]=1[CH:26]=[O:27]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 18668938HCID 18668938, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 43936882-(Tributylstannyl)furanCatalyst

Procedure

Tri(dibenzylideneacetone)-dipalladium (0.18 g, 0.2 mmol), and triphenylphosphine (0.21 g, 0.8 mmol) were dissolved in tetrahydrofuran (60 mL), followed by stirring at room temperature for 30 minutes. Then, 5-bromo-2-fluorobenzaldehyde (0.4 g, 2.0 mmol) and 2-(tributylstannyl)-furan (1.25 mL, 4. 0 mmol) were added thereto, followed by heating under reflux for 10 hours. The mixture was cooled to room temperature, and after the conventional treatment, the residue was purified by silica gel column chromatography (hexane: ethyl acetate=8:1), to give 2-fluoro-5-(2-furyl)benzaldehyde (0.38 g, 100%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 10 hours
  3. temperatureThe mixture was cooled to room temperature
  4. customafter the conventional treatment, the residue was purified by silica gel column chromatography (hexane: ethyl acetate=8:1)

Sources & evidence

ORD record
ord-28c4b9b06f454fdcb5ebfd55dc21269e
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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