Ethyl bromoacetate → HCID 54510282, compound

HRID 1608103Notes

Reaction equation

HRID 1608103 reaction equation
[OH:1][C:2]1[C:3]([Br:13])=[C:4]([C:8]([Br:12])=[CH:9][C:10]=1[Br:11])[C:5]([NH2:7])=[O:6].[Na].Br[CH2:16][C:17]([O:19][CH2:20]C)=[O:18]>CO>[CH3:20][O:19][C:17](=[O:18])[CH2:16][O:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([Br:12])=[C:4]([C:5](=[O:6])[NH2:7])[C:3]=1[Br:13]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545SodiumHCID 19848363HCID 19848363, compound

Product 1

HCID 54510282HCID 54510282, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

35.5 g (95 mmol) of 3-hydroxy-2,4,6-tribromobenzamide is suspended in 150 ml of methanol and dissolved by adding 2.18 g (95 mmol) of sodium. The mixture is combined with 17.5 g (104 mmol) of ethyl bromoacetate and maintained under reflux for three hours. After several hours of agitation, the crystallized product is vacuum-filtered, washed with a small amount of ice-cold methanol, and dried at b 60° C., thus obtaining 37.2 g (88% of theory) of 3-carbamoyl-2,4,6tribromophenoxyacetic acid methyl ester, mp 231°-233° C.

Workup

  1. dissolutiondissolved
  2. temperaturemaintained
  3. temperatureunder reflux for three hours
  4. waitAfter several hours of agitation
  5. filtrationthe crystallized product is vacuum-filtered
  6. washwashed with a small amount of ice-cold methanol
  7. customdried at b 60° C.

Sources & evidence

ORD record
ord-c56307b829d142da8d2617642903d4a9
Source dataset
uspto-grants-1989_09
Patent number
US04869913

Reaction notes

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