Toluene → Methyl 3'-nitro[1,1'-biphenyl]-4-carboxylate

HRID 1449506Notes

Reaction equation

HRID 1449506 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=O)=[CH:4][CH:3]=1.[C:12](=[O:15])([O-])[O-:13].[Na+].[Na+].[N+:18]([C:21]1[CH:22]=C(OB(O)O)C=[CH:25][CH:26]=1)([O-:20])=[O:19].[C:31]1(C)C=CC=CC=1>CO.C(Cl)(Cl)Cl>[N+:18]([C:21]1[CH:22]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:12]([O:13][CH3:31])=[O:15])=[CH:7][CH:6]=2)[CH:9]=[CH:25][CH:26]=1)([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 74654Benzeneacetic acid, 4-bromo-HCID 18508824HCID 18508824, compound

Product 1

HCID 2753361Methyl 3'-nitro[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

In 60 ml of toluene was dissolved 6.4 g of 4-bromophenylacetic acid. To the solution were added 1.04 g of tetrakistriphenylphosphine palladium and 30 ml of 2M sodium carbonate aqueous solution. To the mixture was added the solution of 5.0 g 3-nitrophenylboric acid in 15 ml of methanol under a stream of nitrogen, followed by stirring at 80° C. for 11 hours. The reacton mixture was diluted with chloroform and filtered by Celite. The organic layer was separated and washed with 2M sodium carbonate aqueous solution and dried over anhydrous magnesium sulfate. After removing the solvent, the residue was dissolved in methanol under heating. The mixture was treated with active carbon and cooled to precipitate crystals. The crystals were collected by filtration and dried over anhydrous magnesium sulfate to yield 3.8 g of the titled compound.

Workup

  1. filtrationfiltered by Celite
  2. customThe organic layer was separated
  3. washwashed with 2M sodium carbonate aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. dissolutionthe residue was dissolved in methanol
  7. temperatureunder heating
  8. additionThe mixture was treated with active carbon
  9. temperaturecooled
  10. customto precipitate crystals
  11. filtrationThe crystals were collected by filtration
  12. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-a6f009f902204abfb883d5ca0f4b0119
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

Loading…