HCID 14770832, compound → HCID 14770833, compound

HRID 1651573Notes

Reaction equation

HRID 1651573 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)=[C:4]([F:15])[CH:3]=1>C1COCC1.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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[C:4]([F:15])[CH:3]=1

Participants

4

Reactant 1

HCID 14770832HCID 14770832, compound

Product 1

HCID 14770833HCID 14770833, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 16.4 g (60.2 mmol) of 3-(4-bromo-2,5-difluorophenyl)-2-cyclopentenone in 400 ml of THF was hydrogenated over 2.0 g of Wilkinson's catalyst at 25° C. for 18 hours. The solution was concentrated to a brown oil which was chromatographed on silica gel (E. Merck-230-400 Mesh) to remove the catalyst. The residue obtained was triturated with hexane, and the solids were filtered, washed with hexane, and dried to give 15.2 g (93%) of the title compound; mp 63°-65° C.

Workup

  1. concentrationThe solution was concentrated to a brown oil which
  2. customwas chromatographed on silica gel (E. Merck-230-400 Mesh)
  3. customto remove the catalyst
  4. customThe residue obtained
  5. customwas triturated with hexane
  6. filtrationthe solids were filtered
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-45b4290656ff4535a3d91d802e9a44ef
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

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