1251459-19-4 → HCID 66678168, compound

HRID 2410507Notes

Reaction equation

HRID 2410507 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:18])[C:5]([F:17])=[C:6]([CH:16]=1)[O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[Cu][C:20]#[N:21]>CN(C=O)C>[C:20]([C:2]1[CH:3]=[C:4]([F:18])[C:5]([F:17])=[C:6]([CH:16]=1)[O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:21]

Participants

4

Reactant 2

HCID 666786441251459-19-4HCID 178418546HCID 178418546, compound3×

Product 1

HCID 66678168HCID 66678168, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 4-(5-bromo-2,3-difluorophenoxy)butanoate (2.9 g, 9.0 mmol) in anhydrous DMF (30 mL) was added copper(I) cyanide (1.6 g, 18.0 mmol) under nitrogen atmosphere. The resulting mixture was heated to 120° C. for 16 hours. Additional amount of copper(I) cyanide (0.8 g, 9.0 mmol) was added and the reaction mixture was stirred at 120° C. for 24 hours. A second additional amount of copper(I) cyanide (0.8 g, 9.0 mmol) was added. After 24 additional hours at 120° C., the reaction mixture was cooled down and filtered through a pad of Celite, which was rinsed with EtOAc. The organic layer was washed many times with an aqueous solution of NH4OH and brine, dried (MgSO4) and concentrated under vacuum affording the title compound as a beige solid (2.29 g, 95%). HPLC (Method A) Rt 4.73 min (Purity: 84.4%).

Workup

  1. temperatureAfter 24 additional hours at 120° C., the reaction mixture was cooled down
  2. filtrationfiltered through a pad of Celite, which
  3. washwas rinsed with EtOAc
  4. washThe organic layer was washed many times with an aqueous solution of NH4OH and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-eab96c39e3294c739001925c13ab71d5
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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