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

HRID 443448

反応式

HRID 443448 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ef1a9bcd15e49589cf3dd7213991fb6
出典データセット
uspto-grants-1981_04
特許番号
US04260620

関連ノート

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