Potassium Phosphate, Tribasic → 9-(4-Methylnaphth-1-yl)-10-(4-trimethylsilyinaphthyl)anthracene

HRID 2400239Notes

Reaction equation

HRID 2400239 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH3:23][Si:24]([CH3:39])([CH3:38])[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28](B(O)O)=[CH:27][CH:26]=1.[CH3:40][C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]([C:51]2[C:52]3[C:57]([CH:58]=[C:59]4[C:64]=2[CH:63]=[CH:62][CH:61]=[CH:60]4)=[CH:56][CH:55]=[CH:54][CH:53]=3)=[CH:43][CH:42]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.O1CCOCC1>[CH3:40][C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]([C:51]2[C:64]3[C:59]([C:58]([C:28]4[C:29]5[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:25]([Si:24]([CH3:39])([CH3:38])[CH3:23])=[CH:26][CH:27]=4)=[C:57]4[C:52]=2[CH:53]=[CH:54][CH:55]=[CH:56]4)=[CH:60][CH:61]=[CH:62][CH:63]=3)=[CH:43][CH:42]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 577025649-(4-Methylnaphth-1-yl)anthraceneHCID 598611964-Trimethylsilyinaphth-1-ylboronic acid

Product 1

HCID 598612119-(4-Methylnaphth-1-yl)-10-(4-trimethylsilyinaphthyl)anthracene

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

1.78 g (5.6 mmol) of tri-o-tolylphosphine and 0.2 g (0.9 mmol) of palladium acetate are added to a vigorously stirred, degassed suspension of 22.8 g (93.3 mmol) of 4-trimethylsilyinaphth-1-ylboronic acid, 37.4 g (93.3 mmol) of 9-(4-methylnaphth-1-yl)anthracene and 90 g (230 mmol) of tripotassium phosphate in a mixture of 575 ml of water, 100 ml of dioxane and 860 ml of toluene, and the mixture is refluxed for 60 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and once with 200 ml of saturated aqueous sodium chloride solution and subsequently dried over magnesium sulfate. After the desiccant has been filtered off, the organic phase is evaporated to dryness under reduced pressure in a rotary evaporator. The grey residue obtained in this way is recrystallised from dioxane. The deposited crystals are filtered off with suction, washed with 50 ml of ethanol and subsequently dried under reduced pressure; yield: 38 g, 79% of theory; purity: 99.9% according to HPLC.

Workup

  1. customdegassed
  2. temperaturethe mixture is refluxed for 60 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 200 ml of water
  6. dry with materialonce with 200 ml of saturated aqueous sodium chloride solution and subsequently dried over magnesium sulfate
  7. filtrationAfter the desiccant has been filtered off
  8. customthe organic phase is evaporated to dryness under reduced pressure in a rotary evaporator
  9. customThe grey residue obtained in this way
  10. customis recrystallised from dioxane
  11. filtrationThe deposited crystals are filtered off with suction
  12. washwashed with 50 ml of ethanol
  13. customsubsequently dried under reduced pressure

Sources & evidence

ORD record
ord-b563cb31190f4d76bd2fd008dd292eda
Source dataset
uspto-grants-2014_08
Patent number
US08795847B2

Reaction notes

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