Ethyl bromoacetate → HCID 13116829, compound

HRID 1731622Notes

Reaction equation

HRID 1731622 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([Cl:25])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(#N)C>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([Cl:25])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH:9]([CH3:13])[C:10]([O:12][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:11]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13391436HCID 13391436, compound

Product 1

HCID 13116829HCID 13116829, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 41.0 g (0.104 mol) of the R enantiomer of 2-[3-(2,6-dichloro-4-trifluoromethyl-phenoxy)phenoxy]-propionic acid, 15.8 g (0.114 mol) of potassium carbonate and 17.4 g (0.104 mol) of ethyl bromoacetate in 104 ml of acetonitrile was heated under reflux for 1 hour. Thereafter, working-up was carried out by filtering the reaction mixture under suction, evaporating down the filtrate, taking up the remaining residue in methylene chloride, and washing this solution once with water, drying it and then evaporating it down. The remaining residue was freed from residues of volatile constituents by gentle heating in a high vacuum. In this manner, 34.9 g (70% of theory) of the R enantiomer of (ethoxycarbonyl)-methyl 2-[3-(2,6-dichloro-4-trifluoromethylphenoxy)-phenoxy]-propionate were obtained in the form of a liquid having a refractive index nD20 =1.5190.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. filtrationby filtering the reaction mixture under suction
  4. customevaporating down the filtrate
  5. washwashing this solution once with water
  6. customdrying it
  7. customevaporating it down
  8. temperatureby gentle heating in a high vacuum

Sources & evidence

ORD record
ord-7904c68e05694a8687d3c30ba359e7ce
Source dataset
uspto-grants-1986_11
Patent number
US04622415

Reaction notes

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