Azobisisobutyronitrile → Methyl 2-bromo-2-[3-(trifluoromethyl)phenyl]acetate

HRID 443448

Reaktionsgleichung

Reaktionsgleichung von HRID 443448
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>[Br:16][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:4]=1)[C:10]([O:12][CH3:13])=[O:11]

Komponenten

6

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 2734603Methyl (3-(trifluoromethyl)phenyl)acetate

Produkt 1

HCID 19796654Methyl 2-bromo-2-[3-(trifluoromethyl)phenyl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To the solution of 21.8 g of methyl m-trifluoromethylphenylacetate in 450 ml of carbon tetrachloride a portion of 18.7 g of N-bromosuccinimide is added along with several drops of triethylamine and a pinch of azobisisobutyronitrile. The mixture is warmed to reflux with a 250 watt incandescent bulb and a precipitate is formed. Thereupon the reminder of N-bromosuccinimide is added, the light removed and the solution stirred for 3 hours. It is cooled in an ice bath and the solid formed removed by filtration. The filtrate is evaporated the residue dissolved in diethyl ether-water and the organic phase washed with aqueous sodium bicarbonate and water. It is dried, evaporated, the residue distilled and the fraction boiling at 85°-88°/0.4 mmHg collected, to yield the methyl α-bromo-m-trifluoromethylphenylacetate.

Aufarbeitung

  1. temperatureThe mixture is warmed
  2. temperatureto reflux with a 250 watt incandescent bulb
  3. customa precipitate is formed
  4. customthe light removed
  5. temperatureIt is cooled in an ice bath
  6. customthe solid formed
  7. customremoved by filtration
  8. customThe filtrate is evaporated the residue
  9. dissolutiondissolved in diethyl ether-water
  10. washthe organic phase washed with aqueous sodium bicarbonate and water
  11. customIt is dried
  12. customevaporated
  13. distillationthe residue distilled
  14. customthe fraction boiling at 85°-88°/0.4 mmHg collected

Quellen und Nachweise

ORD-Eintrag
ord-0ef1a9bcd15e49589cf3dd7213991fb6
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04260620

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