Bromopentafluorobenzene → 3-[(2,3,4,5,6-Pentafluorophenyl)ethynyl]aniline

HRID 1030868

反応式

HRID 1030868 の反応式
Br[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[NH2:13][C:14]1[CH:15]=[C:16]([C:20]#[CH:21])[CH:17]=[CH:18][CH:19]=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:12][C:3]1[C:4]([F:11])=[C:5]([F:10])[C:6]([F:9])=[C:7]([F:8])[C:2]=1[C:21]#[C:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[NH2:13]

参加物

6

反応物 2

HCID 9578BromopentafluorobenzeneHCID 104682Benzenamine, 3-ethynyl-

生成物 1

HCID 198210823-[(2,3,4,5,6-Pentafluorophenyl)ethynyl]aniline収率 50%

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
70 °C

実験手順

A multinecked flash as described in Example 1 was charged with 5.0 g (0.020 mol) of bromopentafluoro-benzene, 2.37 g (0.020 mol) of 3-aminophenylacetylene, 0.096 g (0.137 mmol) of bis(triphenylphosphine) palladium II chloride, 0.148 g (0.564 mmol) of triphenylphosphine, and 0.06 g (0.315 mmol) of cuprous iodide. The reaction mixture was heated at 70° C. for 40 hours after which gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble triethylamine hydrobromide salt by-product followed by concentration of the filtrate gave 5.7 g, (0.02 mol) of crude product as a yellow solid. Short path distillation of the crude under reduced pressure gave 2.84 g (0.010 mol, 50% yield) of the product as a colorless liquid that crystallized on standing.

後処理

  1. customthe reaction
  2. temperatureThe product mixture was cooled to room temperature
  3. filtrationFiltration of the insoluble triethylamine hydrobromide salt by-product
  4. customgave 5.7 g, (0.02 mol) of crude product as a yellow solid
  5. distillationShort path distillation of the crude under reduced pressure

出典と根拠

ORDレコード
ord-8f5f3815000a48febbaff23a56453646
出典データセット
uspto-grants-1992_04
特許番号
US05107026

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