Ethanol → 10,10-dimethyl-12-(2-nitrophenyl)-10H-indeno[2,1-b]triphenylene

HRID 716599Notes

Reaction equation

HRID 716599 reaction equation
[CH3:1][C:2]1([CH3:36])[C:26]2[C:6]([CH:7]=[C:8]3[C:25]=2[CH:24]=[C:23]2[C:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=42)=[CH:9]3)=[CH:5][C:4](B2OC(C)(C)C(C)(C)O2)=[CH:3]1.Br[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N+:44]([O-:46])=[O:45].C([O-])([O-])=O.[Na+].[Na+].CCO>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:36])[C:26]2[C:6]([CH:7]=[C:8]3[C:25]=2[CH:24]=[C:23]2[C:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=42)=[CH:9]3)=[CH:5][C:4]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[N+:44]([O-:46])=[O:45])=[CH:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 113411-Bromo-2-nitrobenzeneHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 11825360810,10-dimethyl-12-(2-nitrophenyl)-10H-indeno[2,1-b]triphenyleneYield 58.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9.5 g (20.2 mmol) of 2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4.3 g (21 mmol) of 1-bromo-2-nitrobenzene, 0.44 g (0.4 mmol) of tetrakis(triphenyl phosphine)palladium, 30 ml of 2M Na2CO3, 40 ml of EtOH and 80 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. overnight. After finishing the reaction, the mixture was allowed to cool to room temperature. The solution was extracted with 250 ml of ethyl acetate and 1000 ml of water. The organic layer was dried with anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica (Hx-EA) to give product 5.5 g (58%).

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe solution was extracted with 250 ml of ethyl acetate and 1000 ml of water
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica (Hx-EA)

Sources & evidence

ORD record
ord-ae39e380d3f94dee827b68c4b7e4e173
Source dataset
uspto-grants-2015_11
Patent number
US09190619B2

Reaction notes

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