Ethyl bromoacetate → HCID 87091406, compound

HRID 1505457Notes

Reaction equation

HRID 1505457 reaction equation
[H-].[Na+].[F:3][CH:4]([F:13])[C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[Cl-].[NH4+]>C1COCC1>[F:3][CH:4]([F:13])[C:5]([CH:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:12]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 87091406HCID 87091406, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.52 g (14.296 mmol) of sodium hydride (60% in mineral oil) was initially charged in THF (30 ml), and at 0° C. a solution of 2.00 g (11.437 mmol) of ethyl 4,4-difluoro-3-oxobutyrate in THF (20 ml) was then added dropwise. After warming to RT and a further 30 min at this temperature, 2.865 g (17.156 mmol) of ethyl bromoacetate in THF (15 ml) were added and the mixture was then heated at reflux overnight. After cooling, saturated aqueous ammonium chloride solution was added and the mixture was then extracted three times with ethyl acetate. The combined organic phases were dried with sodium sulphate, filtered and concentrated. After 5 min at high vacuum, the title compound obtained in this manner (3.00 g, about 50% pure) was used without further purification for the next step.

Workup

  1. additionwere added
  2. temperaturethe mixture was then heated
  3. temperatureat reflux overnight
  4. temperatureAfter cooling
  5. extractionthe mixture was then extracted three times with ethyl acetate
  6. dry with materialThe combined organic phases were dried with sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9ac756064be74b23b9a0cc2eec9c6b82
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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