Potassium Carbonate → HCID 58050240, compound

HRID 1676875Notes

Reaction equation

HRID 1676875 reaction equation
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:9]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[S:14][C:13]=2[C:12](B(O)O)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:9]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[S:14][C:13]=2[C:12]([C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[NH2:4])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119922-BromoanilineHCID 2734329Dibenzothiophene-4-boronic acid

Product 1

HCID 58050240HCID 58050240, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 300 ml round-bottom flask equipped with reflux condenser and magnetic stirrer was charged with 2-bromoaniline (8.00 g, 46.5 mmol), 4-dibenzothiopheneboronic acid (10.5 g, 46.5 mmol), potassium carbonate (20 g, saturated solution in water), tetrakis(triphe-nylphoshine)palladium (0) (500 mg) and 100 ml of toluene. The reaction mixture was refluxed overnight under nitrogen atmosphere, filtered through silica plug and evaporated. Product was purified by column chromatography on silica gel, eluent hexane/ethyl acetate 4/1 mixture, providing 2-(dibenzo[b,d]thiophen-4-yl)aniline (10.1 g) as yellow oil.

Workup

  1. customThe 300 ml round-bottom flask equipped
  2. temperaturewith reflux condenser and magnetic stirrer
  3. temperatureThe reaction mixture was refluxed overnight under nitrogen atmosphere
  4. filtrationfiltered through silica plug
  5. customevaporated
  6. customProduct was purified by column chromatography on silica gel, eluent hexane/ethyl acetate 4/1 mixture

Sources & evidence

ORD record
ord-86c7f6f193274d8c8ce3018179fd8f68
Source dataset
uspto-grants-2011_08
Patent number
US08007927B2

Reaction notes

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