Ethyl bromoacetate → HCID 54416269, compound

HRID 1248112Notes

Reaction equation

HRID 1248112 reaction equation
[OH:1][C:2]1[C:3]([Cl:12])=[C:4]([C:7]([Cl:11])=[CH:8][C:9]=1[Cl:10])[C:5]#[N:6].[Na].Br[CH2:15][C:16]([O:18][CH2:19]C)=[O:17]>CO>[CH3:19][O:18][C:16](=[O:17])[CH2:15][O:1][C:2]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[C:4]([C:5]#[N:6])[C:3]=1[Cl:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545Sodium2×HCID 19848359HCID 19848359, compound

Product 1

HCID 54416269HCID 54416269, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22.5 g (0.1 mol) of 3-hydroxy-2,4,6-trichlorobenzonitrile are dissolved in 240 ml of methanol with the addition of 2.3 g (0.1 mol) of metallic sodium. To the resultant suspension of the sodium salt is added 12.15 ml (0.11 mol) of ethyl bromoacetate, and the reaction mixture is heated to reflux until solution is complete. After filtration over active carbon, the solution is cooled and stirred for several hours in an ice bath. The resultant crystalline precipitate is vacuum-filtered, washed with a little ice-cold methanol and dried at 50° C., to produce 19 g (64.5% of theory) of 3-cyano-2,4,6-trichlorophenoxyacetic acid methyl ester as a white powder, mp 110°-112° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux until solution
  3. filtrationAfter filtration over active carbon
  4. temperaturethe solution is cooled
  5. filtrationThe resultant crystalline precipitate is vacuum-filtered
  6. washwashed with a little ice-cold methanol
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-6c8d60f74f604d0fa439100039b3ecf1
Source dataset
uspto-grants-1985_06
Patent number
US04522839

Reaction notes

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