Potassium Carbonate → HCID 58050240, compound

HRID 2273522Notes

Reaction equation

HRID 2273522 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(triphenylphoshine)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-e12d2b339ba84e8487186c25dac42d24
Source dataset
uspto-grants-2015_09
Patent number
US09123903B2

Reaction notes

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