Triethylamine → 3-(3,4-Difluoro-phenylethynyl)-phenylamine

HRID 1030867

反応式

HRID 1030867 の反応式
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[NH2:17][C:18]1[CH:19]=[C:20]([C:24]#[CH:25])[CH:21]=[CH:22][CH:23]=1>CCOCC.[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>[F:1][C:2]1[CH:3]=[C:4]([C:25]#[C:24][C:20]2[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=2)[NH2:17])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 676754-Bromo-1,2-difluorobenzeneHCID 104682Benzenamine, 3-ethynyl-

生成物 1

HCID 198210783-(3,4-Difluoro-phenylethynyl)-phenylamine収率 38.5%

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 flask as described in Example 1 was charged with 5.0 g (0.026 mol) of 3,4-difluorobromobenzene, 50 ml of dried, degassed triethylamine, 3.0 g (0.026 mol) of 3-aminophenylacetylene, 0.07 g (0.1 mmol) of bis(triphenylphosphine) palladium II chloride, 0.1 g (0.38 mmol) of triphenylphosphine, and 0.02 g (0.1 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 36 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 50 ml of ether. Filtration of the insoluble triethylamine hydrobromide salt by-product followed by concentration of the filtrate gave the crude product (4.2 g, 78% yield) as a off-white solid. Short path distillation of the crude product under reduced pressure gave 2.38 g (0.01 mol, 38% yield) of the purified product as a colorless liquid which crystallized on standing.

後処理

  1. customA multinecked flask as described in Example 1
  2. customof dried
  3. customthe reaction
  4. temperatureThe product mixture was cooled to room temperature
  5. filtrationFiltration of the insoluble triethylamine hydrobromide salt by-product
  6. customgave the crude product (4.2 g, 78% yield) as a off-white solid
  7. distillationShort path distillation of the crude product under reduced pressure

出典と根拠

ORDレコード
ord-a47d3c9b012e4946870460f490c5eda2
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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