Ethyl Acetate → HCID 18329869, compound

HRID 2271041Notes

Reaction equation

HRID 2271041 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][C:3]=1[F:10].[CH3:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH3:11])=[CH:4][C:3]=1[F:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzene

Product 1

HCID 18329869HCID 18329869, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step A (ca. 42 mmol) in 50 mL of dimethylformamide was added 2-methylimidazole (3.47 g, 82.1 mmol) and potassium carbonate (7.53 g, 54.6 mmol). After stirring for two hours, the mixture was poured into EtOAc and washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting solid was taken up in 100 mL of EtOAc, and excess HCl gas was bubbled through the solution. The precipitate was removed by filtration, partitioned between dichloromethane and dilute NaHCO3 solution, and the water phase was extracted repeatedly with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide the desired product as a pale yellow oil.

Workup

  1. washwashed with saturated NaHCO3 solution and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customexcess HCl gas was bubbled through the solution
  6. customThe precipitate was removed by filtration
  7. custompartitioned between dichloromethane and dilute NaHCO3 solution
  8. extractionthe water phase was extracted repeatedly with dichloromethane
  9. dry with materialThe combined organic layers were dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a42ba15fb62a4aa68d5ded1b30816d22
Source dataset
uspto-grants-2001_12
Patent number
US06333335B1

Reaction notes

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