1-Chloro-4-nitrobenzene → 4-Nitro-1,1'-biphenyl

HRID 382109Notes

Reaction equation

HRID 382109 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

Product 1

HCID 71144-Nitro-1,1'-biphenylYield 98.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 27342152-(Di-tert-butylphosphino)biphenylCatalyst

Procedure

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 1-chloro-4-nitrobenzene (158 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was scaled with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 196 mg (98%) of the title compound.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. customhad been completely consumed
  6. additionThe reaction mixture was then diluted with ether (30 mL)
  7. filtrationfiltered through celite
  8. concentrationconcentrated
  9. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-122226b367d341bc82aa495cf471ea88
Source dataset
uspto-grants-2001_10
Patent number
US06307087B1

Reaction notes

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