Cesium carbonate → 1-{3-Chloro-5-(2-naphthyl)phenyl}-6-(4-methylphenyl)pyrene

HRID 1914402Notes

Reaction equation

HRID 1914402 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][C:16]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][C:16]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:3]=[C:2]([C:34]2[CH:33]=[CH:32][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 2734375(Naphthalen-2-yl)boronic acidHCID 861013811-(3,5-Dichlorophenyl)-6-(4-methylphenyl)pyrene

Product 1

HCID 861012891-{3-Chloro-5-(2-naphthyl)phenyl}-6-(4-methylphenyl)pyreneYield 37.6%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixed solution of 0.88 g of 1-(3,5-dichlorophenyl)-6-(4-methylphenyl)pyrene, 0.35 g of 2-naphthylboronic acid, 2.9 g of cesium carbonate, 58 mg of (tris-t-butylphosphine)tetrafluoroborate, 0.12 g of bis(dibenzylideneacetone)palladium(0) and 20 ml of 1,4-dioxane was heated and stirred under a nitrogen gas stream at 90° C. for 4 hours. The solution was cooled to room temperature and 50 ml of water was poured into the solution, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 0.40 g of 1-{3-chloro-5-(2-naphthyl)phenyl}-6-(4-methylphenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 100 ml of dichloromethane
  3. washThe organic layer was washed twice with 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe concentrate was purified by silica gel column chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-e4a1285f71d74e69856a95424d49a357
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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