Potassium Phosphate, Tribasic → 9,10-Bis(1,2,3,4-tetrahydro-1,4-methanonaphth-5-yl)anthracene

HRID 1190774

Reaction equation

HRID 1190774 reaction equation
C1(P(C2CCCCC2)C2(OC)[CH2:13][CH:12]=[CH:11][C:10](OC)=[C:9]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)CCCCC1.Br[C:31]1[C:32]2[C:37]([C:38](Br)=[C:39]3[C:44]=1[CH:43]=[CH:42][CH:41]=[CH:40]3)=[CH:36][CH:35]=[CH:34][CH:33]=2.[CH:46]12[CH2:59][CH:49]([C:50]3[C:51](B(O)O)=[CH:52][CH:53]=[CH:54][C:55]=31)[CH2:48][CH2:47]2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O>[CH:46]12[CH2:59][CH:49]([C:50]3[C:55]1=[CH:54][CH:53]=[CH:52][C:51]=3[C:31]1[C:32]3[C:37]([C:38]([C:21]4[CH:20]=[CH:19][CH:18]=[C:17]5[C:16]=4[CH:9]4[CH2:10][CH:11]5[CH2:12][CH2:13]4)=[C:39]4[C:44]=1[CH:43]=[CH:42][CH:41]=[CH:40]4)=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:48][CH2:47]2

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 682269,10-DibromoanthraceneHCID 576945921,2,3,4-Tetrahydro-1,4-methanonaphthalene-5-boronic AcidHCID 665453372-Dicyclohexylphosphino-2,6-dimethoxybiphenyl

Product 1

HCID 576946619,10-Bis(1,2,3,4-tetrahydro-1,4-methanonaphth-5-yl)anthracene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

915 my (1 mmol) of tris(dibenzylidenacetone)dipalladium(0) and 821 mg (2 mmol) of 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl are added to a suspension of 16.8 g (50 mmol) of 9,10-dibromoanthracene, 21.6 g (115 mol) of 1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-boronic acid and 66.9 g (315 mmol) of tripotassium phosphate in 400 ml of anhydrous toluene, and the mixture is refluxed for 16 h. After the reaction mixture has been cooled, 400 ml of water are added, and the precipitate is filtered off with suction, washed three times with 200 ml of water each time, washed three times with 200 ml of ethanol each time, dried under reduced pressure and subsequently chromatographed on silica gel (eluent heptane/toluene 8:2, v/v, column temperature 500C). Sublimation: p=1×10−5 mbar, 300° C. Yield: 13.1 g (28 mmol), 56.6% of theory; purity: 99.5% according to 1H-NMR (including all isomers).

Workup

  1. temperaturethe mixture is refluxed for 16 h
  2. temperatureAfter the reaction mixture has been cooled
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed three times with 200 ml of water each time
  5. washwashed three times with 200 ml of ethanol each time
  6. customdried under reduced pressure
  7. customsubsequently chromatographed on silica gel (eluent heptane/toluene 8:2, v/v, column temperature 500C)
  8. customp=1×10−5 mbar, 300° C

Sources & evidence

ORD record
ord-8b5ecce045a94954bbbd1177d97df5e4
Source dataset
uspto-grants-2014_03
Patent number
US08679645B2

Linked notes

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