Ethyl bromoacetate → HCID 19836754, compound

HRID 1638541Notes

Reaction equation

HRID 1638541 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[H-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][O:7][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 119232-Nitrobenzyl alcoholHCID 24758Sodium hydride

Product 1

HCID 19836754HCID 19836754, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

20 g o-nitro benzylalcohol and 21.7 ml ethyl bromoacetate was dissolved in 250 ml dry DMF. Portions of 55-60% sodium hydride were added to this solution under stirring over one hour until a total amount of 8.5 g had been added. The mixture was left overnight at room temperature and then heated to 150° C. under stirring for 2 hours. The mixture was then evaporated and the residue was partitioned between diethylether and water. The organic phase was evaporated to give 14 g ethyl (o-nitro-benzyloxy)acetate as an oil.

Workup

  1. additionhad been added
  2. waitThe mixture was left overnight at room temperature
  3. stirringunder stirring for 2 hours
  4. customThe mixture was then evaporated
  5. customthe residue was partitioned between diethylether and water
  6. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-1036d742fd644d2daff7e06a9c845a7b
Source dataset
uspto-grants-1989_11
Patent number
US04880799

Reaction notes

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