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

HRID 403066

反応式

HRID 403066 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ceefc20bc9a4030bd16717248086541
出典データセット
uspto-grants-2014_06
特許番号
US08747695B2

関連ノート

読み込み中…