Hexane → HCID 13741334, compound

HRID 1043395Notes

Reaction equation

HRID 1043395 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[C:27]1([PH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[Cu]I.C1(C)C=CC=CC=1>[C:23]1([P:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([P:33]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 10796Cesium carbonateHCID 70017DiphenylphosphineHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 13741334HCID 13741334, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

In a three-necked flask, under a nitrogen atmosphere, there were placed 1.22 g (3 mmol) of 4,4′-diiodobiphenyl (product of Tokyo Kasei Kogyo Co., Ltd.), 0.11 g (0.6 mmol) of copper(I) iodide (product of Wako Pure Chemical Industries, Ltd.) and 3.26 g (12 mmol) of cesium carbonate (Wako Pure Chemical Industries, Ltd.). Next, 50 mL of dehydrated toluene (product of Wako Pure Chemical Industries, Ltd.) and 25 mL (9 mmol) of a hexane solution of diphenylphosphine (diphenylphosphine content: 10 mass %, product of Sterm) were added to the flask, and the mixture was heated to reflux for 24 hours. The reaction mixture was then cooled to room temperature and filtered with Celite. After filtration, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (silica gel, hexane:dichloromethane=2:1), to obtain 650 mg 4,4′-bis(diphenylphosphino)biphenyl represented by the following formula (1) (1.2 mmol, 42% yield), as a phosphine ligand.

Workup

  1. customIn a three-necked flask, under a nitrogen atmosphere, there were placed
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 24 hours
  4. filtrationfiltered with Celite
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. custompurified by silica gel column chromatography (silica gel, hexane:dichloromethane=2:1)

Sources & evidence

ORD record
ord-1bc9a4c4d0a14bbda336c5214d710f5f
Source dataset
uspto-grants-2013_10
Patent number
US08563465B2

Reaction notes

Loading…