Hydrochloric Acid → HCID 67478820, compound

HRID 2089192Notes

Reaction equation

HRID 2089192 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[Si]([C:16]([F:19])([F:18])[F:17])(C)(C)C.Cl>C1COCC1.[F-].[Cs+]>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]([OH:11])[C:16]([F:19])([F:18])[F:17])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 27695822-Fluoro-5-formylbenzonitrile

Product 1

HCID 67478820HCID 67478820, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 25953Cesium fluorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoro-5-formyl-benzonitrile (5 g, 33.5 mmol) and CsF (51 mg, 0.335 mmol) in THF (10 mL) were treated with TMSCF3 (4.77 g, 33.5 mmol) at room temperature for 2 hours. The reaction was then treated with 4 N HCl (5 mL) and stirred at room temperature for 30 min. The solvent was removed and the residue was partitioned between ether and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material, purified by silica gel column (hexanes:ethyl acetate 3:1) to afford the title compound as colorless solid (4.5 g, 61%).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ether and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude material
  8. custompurified by silica gel column (hexanes:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-f069295bf5a240aca1dcd15a8e121c35
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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