Ethanol → HCID 85975625, compound

HRID 2174150Notes

Reaction equation

HRID 2174150 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[C:16]1(B(O)O)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:35](O)[CH3:36]>C1(C)C=CC=CC=1.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.C(Cl)Cl.O>[C:16]1([C:2]2[CH:3]=[CH:4][C:5]3[NH:6][C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][C:10]([C:3]2[C:35]3[C:36](=[CH:12][CH:7]=[CH:8][CH:9]=3)[CH:13]=[CH:14][CH:2]=2)=[CH:9][CH:8]=4)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 2748743,6-Dibromocarbazole

Product 1

HCID 85975625HCID 85975625, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
90 °C

Procedure

Firstly, 8.12 g (25.0 mmol) of 3,6-dibromo-carbazole and 9.46 g (55.0 mmol) of 1-Naphthylboronic acid are dissolved in 100 ml of toluene, and then an aqueous solution of 30 ml of 2M sodium carbonate (Na2CO3) and 30.0 ml of ethanol is added to the above-mentioned solution. After the mixed solution is degassed with nitrogen for 30 minutes, 577 mg (0.5 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) is added to the solution under nitrogen and then the solution is heated to 90° C. After reacting for 8 hours, the solution is cooled to room temperature, added and stirred with methylene chloride and deionized water. Then, the extracted organic layer is dried with anhydrous magnesium sulfate (MgSO4), and the solvent is removed by reducing the pressure. The remains are passed through the silica gel column with petroleum ether:methylene chloride (V:V)=2:1 to obtain a white solid of 9.3 g (22.2 mmol, 89% yield) of 3,6-bis(1-naphthyl) carbazole. The specific reaction is shown in the reaction formula (1-A):

Workup

  1. customAfter the mixed solution is degassed with nitrogen for 30 minutes
  2. temperaturethe solution is cooled to room temperature
  3. additionadded
  4. dry with materialThen, the extracted organic layer is dried with anhydrous magnesium sulfate (MgSO4)
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-3d4042d96a1e4b19bb7ba8fe7e404935
Source dataset
uspto-grants-2015_06
Patent number
US09059413B1

Reaction notes

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