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

HRID 1030868

반응식

HRID 1030868 반응식
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]

참가 물질

6

반응물 2

HCID 9578BromopentafluorobenzeneHCID 104682Benzenamine, 3-ethynyl-

생성물 1

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

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 10122028Bis(triphenylphosphine)palladium촉매HCID 3283Diethyl Ether용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8f5f3815000a48febbaff23a56453646
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05107026

연결된 노트

불러오는 중…