Triethylamine → 3-[[3-(Trifluoromethyl)phenyl]ethynyl]aniline

HRID 1030864

反応式

HRID 1030864 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[NH2:19][C:20]1[CH:21]=[C:22]([C:26]#[CH:27])[CH:23]=[CH:24][CH:25]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>[F:9][C:8]([F:11])([F:10])[C:4]1[CH:3]=[C:2]([C:27]#[C:26][C:22]2[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=2)[NH2:19])[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 104682Benzenamine, 3-ethynyl-

生成物 1

HCID 198838763-[[3-(Trifluoromethyl)phenyl]ethynyl]aniline収率 71%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 10122028Bis(triphenylphosphine)palladium触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
65 °C

実験手順

A multinecked round bottom flask fitted with a mechanical stirrer, reflux condenser, and thermometer was flushed and maintained under positive pressure of nitrogen. The flask was charged with 100.0 g (0.44 mol) of 3-bromobenzotrifluoride, 300 ml of dried, degassed triethylamine, 51.5 g (0.44 mol) of 3-aminophenylacetylene, 0.35 g (0.499 mmol) of bis(triphenylphosphine) palladium II chloride, 1.6 g (6.09 mmol) of (triphenylphosphine), and 0.1 g (0.52 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 20 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature followed by the addition of 200 ml of ether. Removal of the triethylamine hydrobromide salt by-product by suction filtration followed by concentration of the filtrate under reduced pressure gave the crude product as a light off-white solid. Short path distillation of the crude product under reduced pressure gave 81.0 g (0.31 mol, 71% yield) of the product as a colorless liquid which crystallized on standing.

後処理

  1. customA multinecked round bottom flask fitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. customthermometer was flushed
  4. temperaturemaintained under positive pressure of nitrogen
  5. customof dried
  6. customthe reaction
  7. temperatureThe product mixture was cooled to room temperature
  8. customRemoval of the triethylamine hydrobromide salt by-product
  9. filtrationby suction filtration
  10. customgave the crude product as a light off-white solid
  11. distillationShort path distillation of the crude product under reduced pressure

出典と根拠

ORDレコード
ord-a015b5de45ec4a52b31986bb48d5b00d
出典データセット
uspto-grants-1992_04
特許番号
US05107026

関連ノート

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