Ethyl bromoacetate → HCID 54089196, compound

HRID 323275Notes

Reaction equation

HRID 323275 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1.C(OCC)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:9]([C:10]#[N:11])([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:28]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 54089196HCID 54089196, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

Combine 4-methoxyphenylacetonitrile (200 g, 1.36 mol) and tetrahydrofuran (500 mL). Cool to about −5° C. Add dropwise a solution of sodium bis(trimethylsilyl)amide (2900 mL, 1 M in tetrahydrofuran, 2.90 mol). 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 (−12° C.) solution of ethyl bromoacetate (459.9 g) in tetrahydrofuran (1800 mL) at such a rate that the temperature of the reaction mixture does not rise above about 15° C. Allow to stir at ambient temperature. After 18 hours, dilute with diethyl ether and extract with water, 10% hydrochloric acid solution, and saturated aqueous solution of sodium bicarbonate. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to obtain a residue. Distill the residue by bulb-to-bulb distillation to give the title compound: bp; 175-185° C. at 1.0 mm Hg.

Workup

  1. additionWhen the addition
  2. temperatureis complete warm the reaction mixture to ambient temperature
  3. customdoes not rise above about 15° C
  4. stirringto stir at ambient temperature
  5. waitAfter 18 hours
  6. extractionextract with water, 10% hydrochloric acid solution, and saturated aqueous solution of sodium bicarbonate
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customto obtain a residue
  11. distillationDistill the residue
  12. distillationby bulb-to-bulb distillation

Sources & evidence

ORD record
ord-3fc5ef9090874162a2a3f7ffca7ef674
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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