Tetrahydrofuran → HCID 22483438, compound

HRID 2182116Notes

Reaction equation

HRID 2182116 reaction equation
[NH4+].[Cl-].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](F)([F:14])[C:9](F)([F:16])[CH:8]=[CH:7]2.C1COCC1>[NH4+].[OH-].[Zn]>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([F:14])=[C:9]([F:16])[CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 22483434HCID 22483434, compound

Product 1

HCID 22483438HCID 22483438, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 14923Ammonium HydroxideSolvent2×

Procedure

A cold solution of 2.3 g of NH4Cl in 10 ml of NH4OH was added to a stirred mixture of 2.00 g (8.45 mmol) of 6-chloro-1,1,2,2-tetrafluoro-1,2-dihydronaphthalene, 5 ml of THF, and 0.84 g (13 mmol) of zinc that was cooled in an ice bath. The mixture was allowed to warm slowly to room temperature. After 22 h, 0.31 g (4.8 mmol) of additional zinc and 3 ml of NH4OH were added. After 24 h reaction time, the zinc was removed by filtration. The phases were separated, and the aqueous layer was extracted three times with hexanes. The combined organic phase was washed twice with brine, dried over MgSO4 and decolorized with activated carbon. The MgSO4 and carbon were filtered off, and the solvent was removed under vacuum. A colorless solid (1.6 g, 7.8 mmol, 92% yield) remained.

Workup

  1. temperaturewas cooled in an ice bath
  2. customAfter 24 h reaction time
  3. customthe zinc was removed by filtration
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted three times with hexanes
  6. washThe combined organic phase was washed twice with brine
  7. dry with materialdried over MgSO4
  8. filtrationThe MgSO4 and carbon were filtered off
  9. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-afe893b01c414a0db79903c04258c59b
Source dataset
uspto-grants-2005_05
Patent number
US06894200B2

Reaction notes

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