Ethyl bromoacetate → HCID 17791214, compound

HRID 323249Notes

Reaction equation

HRID 323249 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1.C(OCC)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C:8]([C:9]#[N:10])([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:27]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2415824-Chlorobenzyl cyanideHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 17791214HCID 17791214, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Combine 4-chlorophenylacetonitrile (50.0 mmol) and tetrahydrofuran (140 mL). Cool to about 5° C. Add dropwise a solution of sodium bis(trimethylsilyl)amide (800 mL, 1 M in tetrahydrofuran, 800 mmol). When the addition is complete, warm the reaction mixture to ambient temperature and allow to stir for 1 hour. Transfer the above solution via cannula into a cooled (−8° C.) solution of ethyl bromoacetate.(84.5 mL, 762 mmol) in tetrahydrofuran (500 mL) at such a rate that the temperature of the reaction mixture does not rise above about 20° C. Allow to stir at ambient temperature. After 18 hours, dilute with diethyl ether (1.5 L) and extract with saturated aqueous solution of ammonium chloride, then water, and then saturated aqueous solution of sodium chloride. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give the title compound. Elemental Analysis calculated for C16H18ClNO4: C 59.35; H 5.60; N 4.33; Found: C 59.27; H 5.54; N 4.33.

Workup

  1. additionWhen the addition
  2. temperaturewarm the reaction mixture to ambient temperature
  3. customdoes not rise above about 20° C
  4. stirringto stir at ambient temperature
  5. waitAfter 18 hours
  6. extractionextract with saturated aqueous solution of ammonium chloride
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e3266dfdae2d4e8a96cb8d7b2012747f
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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