Ethyl bromoacetate → HCID 85879299, compound

HRID 1376101Notes

Reaction equation

HRID 1376101 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([C:15]#[N:16])[CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[Cl-].[NH4+].C(OCC)(=O)C>CN(C)C=O>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:15]#[N:16])[C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])[CH3:25]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 85879296HCID 85879296, compoundHCID 86583716Ammonium chloride ethyl acetate

Product 1

HCID 85879299HCID 85879299, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, stir and cool to 0° C. a solution of N-(4-chloro-2-cyano-phenyl)-2,2,2-trifluoroacetamide (4.80 g, 19.31 mmol) in dimethylformamide (50 mL), and add NaH (0.7 g, 29.1 mmol). Stir the reaction for 1 h at ambient temperature and add ethyl bromoacetate (4.3 mL, 38.77 mmol) by means of a syringe. Stir at 50° C. overnight and then pour the reaction into aqueous ammonium chloride-ethyl acetate. Wash the organic layer with brine (2×'s), dry over MgSO4, filter and evaporate to obtain an oil. Chromatograph the oil eluting with 20% ethyl acetate/heptane and then 30% ethyl acetate/heptane. Concentrate the appropriate fractions and obtain 6.0 g of a solid MS 335(M+H), m.p. 71–73° C.

Workup

  1. stirringStir
  2. customthe reaction for 1 h at ambient temperature
  3. stirringStir at 50° C. overnight
  4. additionpour
  5. washWash the organic layer with brine (2×'s),
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customevaporate
  9. customto obtain an oil
  10. washChromatograph the oil eluting with 20% ethyl acetate/heptane
  11. concentrationConcentrate the appropriate fractions

Sources & evidence

ORD record
ord-aabe368f8f70432eaa4eb7859f69ccaf
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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