Toluene → HCID 18925402, compound

HRID 1289075Notes

Reaction equation

HRID 1289075 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[S:10][CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].[Cl:17][C:18]1[CH:23]=[CH:22][C:21](OB(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>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(O)C>[N+:14]([C:13]1[CH:12]=[CH:11][S:10][C:9]=1[C:21]1[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=1)([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 12014892-Bromo-3-nitrothiopheneHCID 17810664p-Chlorophenylboric acid

Product 1

HCID 18925402HCID 18925402, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To 50 ml of toluene, 1 g of 2-bromo-3-nitrothiophene, 0.75 g of 4-chlorophenylboric acid, 5 ml of a 2M-aqueous potassium carbonate solution and 2 ml of ethanol were added and stirred at room temperature for 30 minutes in a nitrogen atmosphere. Successively 0.28 g of Pd(PPh3)4 was added and heat-refluxed for 2 hours. The aqueous layer was separated from the reaction mixture and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue thus obtained was purified by silica gel column chromatography to obtain 1.1 g of the product as a yellow crystal. The yield was 98%. 1H-NMR(CDCl3, δ value):7.29(1H, d, J=5.9), 7.43(4H, s), 7.66(1H, d, J=5.9)

Workup

  1. temperatureheat-refluxed for 2 hours
  2. customThe aqueous layer was separated from the reaction mixture
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-750d117826394b67817746d1e29961c2
Source dataset
uspto-grants-1998_05
Patent number
US05747518

Reaction notes

Loading…