HCID 18004174, compound → HCID 59695992, compound

HRID 2241845Notes

Reaction equation

HRID 2241845 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9](Br)=[C:10]3[C:15]=1[CH:14]=[C:13]([O:16][CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:12]=[CH:11]3)=[CH:7][C:6]([O:26][CH2:27][CH:28]([CH2:33][CH3:34])[CH2:29][CH2:30][CH2:31][CH3:32])=[CH:5][CH:4]=2.[H-].C([Al+][CH2:41][CH:42]([CH3:44])[CH3:43])C(C)C.[C:45]1([CH3:51])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[C:3]1([C:44]([C:42]2[CH:41]=[CH:22][CH:21]=[CH:20][CH:43]=2)=[CH:51][C:45]2[CH:50]=[CH:49][C:48]([C:2]3[C:3]4[C:8]([C:9]([C:48]5[CH:49]=[CH:50][C:45]([CH:51]=[C:44]([C:14]6[CH:15]=[CH:10][CH:11]=[CH:12][CH:13]=6)[C:42]6[CH:41]=[CH:17][CH:18]=[CH:19][CH:43]=6)=[CH:46][CH:47]=5)=[C:10]5[C:11]=3[CH:12]=[C:13]([O:16][CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:14]=[CH:15]5)=[CH:7][C:6]([O:26][CH2:27][CH:28]([CH2:33][CH3:34])[CH2:29][CH2:30][CH2:31][CH3:32])=[CH:5][CH:4]=4)=[CH:47][CH:46]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 18004174HCID 18004174, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 59695992HCID 59695992, compoundYield 1,187.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added into a 500 ml three-necked flask equipped with a condenser under a gaseous stream of argon were 9,10-dibromo-2,6-di(2-ethylhexyloxy) anthracene 0.6 g (1 mmole), dichlorobis(triphenylphosphine) palladium 0.04 g (5 mole %), diisobutylaluminum hydride/toluene solution 0.1 ml (1 M, 0.1 mmole) and THF 10 ml. After the above-mentioned Grignard reagent was added dropwise to them at room temperature, they were heated and stirred overnight. After the completion of the reaction, the reaction solution was cooled with ice water, the precipitates were filtered and washed with methanol 50 ml followed by acetone 50 ml to give the yellow powder 0.56 g. This was identified as Compound 10 by NMR, IR and field desorption mass spectra measurements (FD-MS) (yield 60%).

Workup

  1. additionAdded into a 500 ml three-necked flask
  2. customequipped with a condenser under a gaseous stream of argon
  3. temperaturethey were heated
  4. customAfter the completion of the reaction
  5. filtrationthe precipitates were filtered
  6. washwashed with methanol 50 ml

Sources & evidence

ORD record
ord-2a1f987398f446249d201859d56748c2
Source dataset
uspto-grants-2010_03
Patent number
US07670506B1

Reaction notes

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