Ethyl bromoacetate → HCID 21460675, compound

HRID 2082495Notes

Reaction equation

HRID 2082495 reaction equation
[F:1][C:2](F)(F)[CH2:3][C:4]([NH2:6])=O.FC1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=CC=1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[C:20]([CH2:19][NH:6][C:4]1[CH:3]=[C:2]([F:1])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15])([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67619889HCID 67619889, compound

Product 1

HCID 21460675HCID 21460675, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve the 2-trifluoromethylacetamide-4-fluorobenzonitrile (1 g, 4.3 mmol) in dimethylformamide (4 mL) under an atmosphere of nitrogen. Add ethyl bromoacetate (0.954 mL, 8.6 mmol), potassium carbonate (1.1 g, 8.6 mmol) and heat to 50° C. for 2.5 hours. Dilute the reaction with ethyl acetate and rinse the organic phase with water. Dry the organic phase, filter and concentrate in vacuo to yield the title compound (1.1 g).

Workup

  1. additionDilute
  2. washrinse the organic phase with water
  3. customDry the organic phase
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-69e29df53d90444985b18058dfb7b7ac
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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