Water → HCID 67059819, compound

HRID 601448Notes

Reaction equation

HRID 601448 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

HCID 67059819HCID 67059819, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e49c8341712a4098bdb96ce32e9bfe59
Source dataset
uspto-grants-2011_03
Patent number
US07902363B2

Reaction notes

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