Cesium carbonate → HCID 86669118, compound

HRID 1041828Notes

Reaction equation

HRID 1041828 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][C:3]=1[CH:9]1[CH2:11][CH2:10]1.[CH2:12]([C:16]1[CH:21]=[CH:20][C:19]([C:22]#[CH:23])=[CH:18][CH:17]=1)[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)[C:37]2[CH:42]=[CH:41]C=C[C:38]=2[C:43]2[C:48](C(C)C)=[CH:47][C:46]([CH:52](C)[CH3:53])=[CH:45][C:44]=2C(C)C)CCCCC1>O1CCOCC1.CC#N.CC#N.Cl[Pd]Cl.O>[CH2:12]([C:16]1[CH:17]=[CH:18][C:19]([C:22]#[C:23][C:2]2[CH:7]=[CH:6][C:5]([C:53]#[C:52][C:46]3[CH:47]=[CH:48][C:43]([CH2:38][CH2:37][CH2:42][CH3:41])=[CH:44][CH:45]=3)=[CH:4][C:3]=2[CH:9]2[CH2:11][CH2:10]2)=[CH:20][CH:21]=1)[CH2:13][CH2:14][CH3:15]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 27751321-Butyl-4-ethynylbenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 57732587HCID 57732587, compound

Product 1

HCID 86669118HCID 86669118, compound

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5 g (26 mmol) of 1,4-dichloro-2-cyclopropylbenzene, 9.4 g (58 mmol) of 1-n-butyl-4-ethynylbenzene, 19 g (58 mmol) of caesium carbonate, 69 mg (0.3 mmol) of bis(acetonitrile)palladium(II) chloride and 382 mg (0.8 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl are dissolved in 80 ml of dioxane under nitrogen and heated at 100° C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography and recrystallised from ethanol, giving the title compound 1 as a solid.

Workup

  1. extractionthe mixture is extracted twice with methyl t-butyl ether (100 ml)
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified by column chromatography
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-66c1f4db14854b308f8a6ebd08273fec
Source dataset
uspto-grants-2013_10
Patent number
US08557142B2

Reaction notes

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