Toluene → HCID 57735330, compound

HRID 1464953Notes

Reaction equation

HRID 1464953 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.[C:19]1(B(O)O)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[CH3:60])C1C=CC=CC=1C.[C:62]1(C)[CH:67]=CC=C[CH:63]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:19]1([C:9]2[CH:8]=[CH:7][C:6]3[C:5](=[O:18])[C:4]4[C:13](=[CH:14][CH:15]=[C:2]([C:56]5[C:55]6[C:54](=[CH:63][CH:62]=[CH:67][CH:60]=6)[CH:59]=[CH:58][CH:57]=5)[CH:3]=4)[C:12](=[O:16])[C:11]=3[CH:10]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 2545321-Naphthaleneboronic acidHCID 109594842,6-Dibromoanthraquinone

Product 1

HCID 57735330HCID 57735330, compound

Reagents, catalysts & solvents 3

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

Procedure

A suspension of 28.7 g (100 mmol) of 2,6-dibromoanthraquinone, 44.7 g (260 mmol) of 1-naphthylboronic acid, 89.2 g (420 mmol) of potassium phosphate, 1.8 g (6 mmol) of tri-o-tolylphosphine and 225 mg (1 mmol) of palladium(II) acetate in a mixture of 200 ml of dioxane, 400 ml of toluene and 500 ml of water is refluxed for 16 h. After cooling, the solid is filtered off with suction, washed three times with 100 ml of water each time and three times with 100 ml of ethanol each time, dried in vacuo and subsequently recrystallised twice from chlorobenzene. Yield: 41.6 g (90 mmol), 90.3% of theory; purity: 99% according to NMR.

Workup

  1. temperatureis refluxed for 16 h
  2. temperatureAfter cooling
  3. filtrationthe solid is filtered off with suction
  4. washwashed three times with 100 ml of water each time and three times with 100 ml of ethanol each time
  5. customdried in vacuo
  6. customsubsequently recrystallised twice from chlorobenzene

Sources & evidence

ORD record
ord-1e4f08c3a6b647268503bba635082e59
Source dataset
uspto-grants-2015_04
Patent number
US08999521B2

Reaction notes

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