Water → HCID 67059819, 화합물

HRID 601448노트

반응식

HRID 601448 반응식
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N+:18]([C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)([O-:20])=[O:19].O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].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>[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

참가 물질

7

반응물 3

HCID 962WaterHCID 124951-Iodo-4-nitrobenzeneHCID 4197992(4-octylphenyl)boronic Acid

생성물 1

HCID 67059819HCID 67059819, 화합물수율 95%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

실험 절차

Tetrakis(triphenylphosphine)palladium (0) (0.30 g, 0.26 mmol) and p-n-octylphenylboronic acid (1.0 g, 4.3 mmol) were sequentially added to a stirred solution of 4-nitroiodobenzene (0.87 g, 3.5 mmol) in 1,2-dimethoxyethane (13 mL) and aqueous sodium carbonate (2 M, 13 mL) under dry nitrogen. The stirred mixture was heated under reflux overnight and cooled. Water was added and the product was extracted into ether (30 3 mL) and the combined ethereal extracts were washed with brine and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by chromatography using a short silica gel column (hexane:ethyl acetate—5:1 to 2:1] to provide 4′-nitro-4-n-octyl-biphenyl as a yellow oil, which solidified upon standing (1.04 g, 95% yield). The solid was used without further purification.

후처리

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. extractionthe product was extracted into ether (30 3 mL)
  5. washthe combined ethereal extracts were washed with brine
  6. dry with materialdried with MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-e49c8341712a4098bdb96ce32e9bfe59
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902363B2

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