Toluene → 9,10-Di(5,6,7,8-tetrahydronaphthalen-1-yl)anthracene

HRID 1190775Notes

Reaction equation

HRID 1190775 reaction equation
C1(C)C=CC=CC=1P([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])C1C=CC=CC=1C.Br[C:24]1[C:25]2[C:30]([C:31](Br)=[C:32]3[C:37]=1[CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:29][CH:28]=[CH:27][CH:26]=2.[C:39]1(B(O)O)[C:48]2[CH2:47][CH2:46][CH2:45][CH2:44][C:43]=2[CH:42]=[CH:41][CH:40]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:60]1(C)[CH:65]=CC=C[CH:61]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:39]1([C:24]2[C:25]3[C:30]([C:31]([C:15]4[C:16]5[CH2:21][CH2:65][CH2:60][CH2:61][C:17]=5[CH:18]=[CH:19][CH:20]=4)=[C:32]4[C:37]=2[CH:36]=[CH:35][CH:34]=[CH:33]4)=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:48]2[CH2:47][CH2:46][CH2:45][CH2:44][C:43]=2[CH:42]=[CH:41][CH:40]=1

Participants

9

Reactant 5

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 682269,10-DibromoanthraceneHCID 80271Tri-o-tolylphosphineHCID 230054155,6,7,8-Tetrahydronaphthalen-1-ylboronic acid

Product 1

HCID 576945849,10-Di(5,6,7,8-tetrahydronaphthalen-1-yl)anthracene

Reagents, catalysts & solvents 3

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

Procedure

688 mg (2.26 mmol) of tri-o-tolylphosphine and then 84 mg (0.37 mmol) of palladium(II) acetate are added to a vigorously stirred, degassed suspension of 12.7 g (37.7 mmol) of 9,10-dibromoanthracene, 17.2 g (97.7 mmol) of (5,6,7,8-tetrahydro-1-naphthyl)boronic acid and 26.6 g (126 mmol) of tripotassium phosphate in a mixture of 230 ml of toluene, 115 ml of dioxane and 170 ml of water, 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, dried over magnesium sulfate and evaporated to dryness under reduced pressure. 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 dried under reduced pressure; yield: 7.5 g, 45% having a purity of 99.8% 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, dried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe grey residue obtained in this way
  9. customis recrystallised from dioxane
  10. filtrationThe deposited crystals are filtered off with suction
  11. washwashed with 50 ml of ethanol
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-e1091abbd9ae45419402d277233f9940
Source dataset
uspto-grants-2014_03
Patent number
US08679645B2

Reaction notes

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