Water → 1-Bromo-4-(4-n-propylphenylethynyl)naphthalene

HRID 403066

반응식

HRID 403066 반응식
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][CH:3]=1.[CH2:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]#[CH:23])=[CH:18][CH:17]=1)[CH2:14][CH3:15].O.CCCCCCC>CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:23]#[C:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:13][CH2:14][CH3:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 8900HeptaneHCID 27751331-Ethynyl-4-propylbenzeneHCID 50736671-Bromo-4-iodonaphthalene

생성물 1

HCID 671178511-Bromo-4-(4-n-propylphenylethynyl)naphthalene

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

15.3 g (43.6 mmol) of 1-iodo-4-bromonaphthalene and 7.25 g (5.3 mmol) of 4-n-propylphenylacetylene are initially introduced in 200 ml of NEt3, 170 mg (0.9 mmol) of copper(I) iodide and 600 mg (0.9 mmol) of bis-(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 30 minutes. The batch is cooled, water and heptane are added, and the phases are separated. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol.

후처리

  1. temperaturethe mixture is refluxed for 30 minutes
  2. temperatureThe batch is cooled
  3. customthe phases are separated
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. customThe residue is purified by column chromatography (SiO2, heptane)
  9. customthe further purification
  10. customis carried out by recrystallisation from isopropanol

출처 및 근거

ORD 기록
ord-4ceefc20bc9a4030bd16717248086541
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08747695B2

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