Potassium Carbonate → HCID 58050240, compound

HRID 2039423Notes

Reaction equation

HRID 2039423 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-3e8eb31ec7b84addada3fee0b613fbb9
Source dataset
uspto-grants-2013_11
Patent number
US08580402B2

Reaction notes

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