Dichloromethane → 1-(3-t-Butylphenyl)-6-(4-methylphenyl)pyrene

HRID 1027323Notes

Reaction equation

HRID 1027323 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:25]([C:29]1[CH:30]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:32]=[CH:33][CH:34]=1)([CH3:28])([CH3:27])[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C)C=O>[C:25]([C:29]1[CH:30]=[C:31]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:32]=[CH:33][CH:34]=1)([CH3:26])([CH3:27])[CH3:28]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 222401372-(3-(tert-Butyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 861013611-Bromo-6-(4-methylphenyl)pyrene

Product 1

HCID 866430241-(3-t-Butylphenyl)-6-(4-methylphenyl)pyreneYield 81.7%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Next, a mixed solution of 4.6 g of 1-bromo-6-(4-methylphenyl)pyrene, 4.9 g of 2-(3-t-butylphenyl)-4,4,5,5-tetramethyl 1,3,2-dioxaborolane, 8.0 g of tripotassium phosphate, 306 mg of PdCl2(dppf).CH2Cl2 and 75 ml of deaerated dimethylformamide was heated with stirring under a nitrogen gas flow at 100° C. for 6 hours. After cooling to room temperature, 100 ml of water was injected, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. The resultant concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 4.3 g of 1-(3-t-butylphenyl)-6-(4-methylphenyl)pyrene.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with 100 ml of dichloromethane
  3. washThe organic layer was washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. concentrationThe resultant concentrate
  7. customwas purified by silica gel column chromatography
  8. customvacuum-dried

Sources & evidence

ORD record
ord-d8980f36b56f42aea53219552aa6cbc0
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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