1,3-Dichloro-5,6-dihydro-4H-cyclopenta(c)thiophen-4-one → HCID 23434091, compound

HRID 1004176Notes

Reaction equation

HRID 1004176 reaction equation
[Cl:1][C:2]1[S:3][C:4](Cl)=[C:5]2[C:9](=[O:10])[CH2:8][CH2:7][C:6]=12.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(O)=O.[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[S:3][C:4]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[F:12])=[C:5]2[C:9](=[O:10])[CH2:8][CH2:7][C:6]=12

Participants

6

Reactant 3

HCID 3156161,3-Dichloro-5,6-dihydro-4H-cyclopenta(c)thiophen-4-oneHCID 516892Sodium BicarbonateHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 23434091HCID 23434091, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 1,3-dichloro-5,6-dihydro-4H-cyclopenta(c)thiophene-4-one (250 mg, 1.21 mmol) in DME (7.5 mL) was added 2-fluorobenzeneboronic acid (177 mg, 1.27 mmol), saturated aqueous NaHCO3 solution (2.5 mL) and bis(triphenylphosphine)palladium(II)chloride (100 mg, 0.14 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 8 hours. The whole was extracted with ethyl acetate (50 mL×2), and the combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane-ethyl acetate (10:1) to provide the subtitle compound (118 mg, 37% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 8 hours
  3. extractionThe whole was extracted with ethyl acetate (50 mL×2)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-73a46329e95345be9237b68a9f74c1a1
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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