Ethanol → HCID 86722507, compound

HRID 879911Notes

Reaction equation

HRID 879911 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH:7]=[C:8]4[C:23]([CH3:25])([CH3:24])[C:22]5[C:17](=[CH:18][CH:19]=[C:20](Br)[CH:21]=5)[C:9]4=[CH:10][C:11]=3[C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CCO>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:27]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:20]1[CH:19]=[CH:18][C:17]2[C:9]3[CH:10]=[C:11]4[C:12]([CH3:16])([CH3:15])[C:13]5[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:14]=5)[C:6]4=[CH:7][C:8]=3[C:23]([CH3:24])([CH3:25])[C:22]=2[CH:21]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 4589187Biphenyl-2-boronic acidHCID 589872862,8-Dibromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene

Product 1

HCID 86722507HCID 86722507, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 14.7 g (31.5 mmol) of 2,8-dibromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene, 6.5 g (33 mmol) of biphenyl-2-ylboronic acid, 0.36 g (0.3 mmol) of tetrakis(triphenylphosphine) palladium, 32 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 9.7 g (17.9 mmol, 57%). 1H NMR (CDCl3, 400 MHz): chemical shift (ppm): 7.78 (d, J=8.0 Hz, 1H), 7.65˜7.61 (m, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.51˜7.21 (m, 10H), 7.18 (s, 2H), 7.08˜6.99 (m, 2H), 1.83 (s, 6H), 1.81 (s, 6H)

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe organic layer was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica (hexane-dichloromethane)

Sources & evidence

ORD record
ord-7d5685335743400b94e0afa49b1df72d
Source dataset
uspto-grants-2015_03
Patent number
US08993130B2

Reaction notes

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