Ethanol → HCID 86720325, compound

HRID 578600Notes

Reaction equation

HRID 578600 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[CH3:18][C:19]1([CH3:53])[C:43]2[C:23]([CH:24]=[C:25]3[CH:42]=[C:41]4[C:28]([C:29]5[C:34]([C:35]6[C:40]4=[CH:39][CH:38]=[CH:37][CH:36]=6)=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:27][C:26]3=2)=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20]1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:12]([C:11]3[CH:10]=[CH:9][C:8]([C:21]4[CH:22]=[C:23]5[C:43]([C:19]([CH3:53])([CH3:18])[CH:20]=4)=[C:26]4[C:25]([CH:42]=[C:41]6[C:28](=[CH:27]4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=4[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:40]6=4)=[CH:24]5)=[CH:7][C:6]=3[C:5]2([CH3:16])[CH3:17])=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 121238762,7-Dibromo-9,9-dimethylfluoreneHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86720325HCID 86720325, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4.9 g (14 mmol) of 2,7-dibromo-9,9-dimethyl-9H-fluorene, 7.53 g (16 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.16 g (0.14 mmol) of Tetrakis(triphenylphosphine)palladium, 11 ml of 2M Na2CO3, 30 ml of EtOH and 65 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. Than 500 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 3.7 g (yield 43%) of yellow product which was recrystallized from toluene.

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered off with suction

Sources & evidence

ORD record
ord-d49a318b4ff94d09ab30effd9abbc00e
Source dataset
uspto-grants-2015_05
Patent number
US09040174B2

Reaction notes

Loading…