Water → 1-Fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthalene

HRID 857607노트

반응식

HRID 857607 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].Br[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:24][C:25]([F:28])([F:27])[F:26])[C:19]=2[F:23])[CH:14]=1.C1(C)C=CC=CC=1.O>CN(C)C=O.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:19]1[C:20]2[C:15](=[CH:14][C:13]([C:11]#[C:10][C:7]3[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][C:18]=1[O:24][C:25]([F:28])([F:27])[F:26]

참가 물질

8

반응물 4

HCID 962WaterHCID 1140TolueneHCID 27751331-Ethynyl-4-propylbenzeneHCID 218701542-Bromo-5-fluoro-6-trifluoromethoxynaphthalene

생성물 1

HCID 218697581-Fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthalene수율 36.6%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

10 g of 4-propyl-1-ethynylbenzene and 19.5 g of 2-bromo-5-fluoro-6-trifluoromethoxynaphthalene were dissolved in 50 ml of N,N-dimethylformamide (DMF). To the solution were then added 50 mg of copper iodide (I) and 100 mg of tetrakis(triphenylphosphine)palladium (0). The reaction mixture was then stirred at room temperature for 5 hours. To the reaction solution was then added toluene. Insoluble matters water removed by filtration. The residue was then washed with water and saturated brine. The solvent was then distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate 9/1), and then recrystallized from ethanol to obtain 8.6 g of 1-fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthalene.

후처리

  1. customremoved by filtration
  2. washThe residue was then washed with water and saturated brine
  3. distillationThe solvent was then distilled off
  4. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate 9/1)
  5. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-ef3929760d114f2eb3d9bca52eaacad3
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07145047B2

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