Toluene → HCID 59695992, compound

HRID 900388Notes

Reaction equation

HRID 900388 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.[C:35]1([CH3:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[H-]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:35]1([C:41]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:41][C:35]2[CH:40]=[CH:39][C:38]([C:2]3[C:3]4[C:8]([C:9]([C:38]5[CH:39]=[CH:40][C:35]([CH:41]=[C:41]([C:3]6[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=6)[C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)=[CH:36][CH:37]=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:37][CH:36]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 166653HydrideHCID 18004174HCID 18004174, compound

Product 1

HCID 59695992HCID 59695992, compoundYield 2,374.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Into a 500 ml flask equipped with a condenser, 0.6 g (1 mmole) of 9,10-dibromo-2,6-di(2-ethylhexyloxy)anthracene, 0.04 g (5% by mole) of dichlorobis(triphenylphosphine)palladium, 0.1 ml (1 M; 0.1 mmole) of a toluene solution of diusobutylaluminum hydride and 10 ml of THF were placed under a stream of argon. After the Grignard reagent prepared above was added dropwise to the obtained solution at the room temperature, the resultant mixture was heated under stirring for one night. After the reaction was completed, the reaction solution was cooled with ice water. The formed crystals were separated by filtration and washed with 50 ml of methanol and 50 ml of acetone successively, and 0.56 g of a yellow powder was obtained. The obtained yellow powder was identified to be Compound (A1) by the measurements in accordance with NMR, IR and the filed desorption mass spectroscopy (FD-MS) (the yield: 60%).

Workup

  1. customInto a 500 ml flask equipped with a condenser
  2. additionabove was added dropwise to the obtained solution at the room temperature
  3. customThe formed crystals were separated by filtration
  4. washwashed with 50 ml of methanol and 50 ml of acetone successively

Sources & evidence

ORD record
ord-a9f8f6d480044b1dbba2578ace46fa7e
Source dataset
uspto-grants-2008_04
Patent number
US07357991B2

Reaction notes

Loading…