2,3-Dichloronitrobenzene → HCID 15175504, compound

HRID 1755509Notes

Reaction equation

HRID 1755509 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P([O-])([O-])([O-])=O.[K+].[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.O1CCCC1>[N+:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 185552,3-DichloronitrobenzeneHCID 62657Potassium Phosphate, TribasicHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 15175504HCID 15175504, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, a one-liter three-necked flask was charged with 75.0 g (390.6 mmol) of 2,3-dichloronitrobenzene, 47.6 g (390.6 mmol) of phenylboric acid, 9.0 g (7.8 mmol) of tetrakis(triphenylphosphine)palladium, 250 mL of tetrahydrofuran, and 518 g (976.5 mmol) of an aqueous tripotassium phosphate solution with 40 wt. % concentration. The mixture was heated under reflux for 8 hours. The reaction mixture was cooled to room temperature, and then separated into an aqueous phase and an organic phase. The organic phase was washed with an aqueous saturated ammonium chloride solution and then with an aqueous saturated sodium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate and then a solvent was distilled off under reduced pressure. The thus-obtained solid was recrystallized from ethanol to give 62.8 g of 2-nitro-6-chlorobiphenyl as a light yellow needle crystal (yield: 680).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customseparated into an aqueous phase
  4. washThe organic phase was washed with an aqueous saturated ammonium chloride solution
  5. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  6. distillationa solvent was distilled off under reduced pressure
  7. customThe thus-obtained solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-b540ac6be46d493aa6d74f2a9160769e
Source dataset
uspto-grants-2015_10
Patent number
US09172045B2

Reaction notes

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