4-Nitro-2',3',4',5',6'-pentafluorobiphenyl → 2',3',4',5',6'-Pentafluoro[1,1'-biphenyl]-4-ylamine

HRID 601453Notes

Reaction equation

HRID 601453 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:11]=2[F:20])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([F:20])=[C:12]([F:19])[C:13]([F:18])=[C:14]([F:17])[C:15]=2[F:16])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 112547604-Nitro-2',3',4',5',6'-pentafluorobiphenyl

Product 1

HCID 159386172',3',4',5',6'-Pentafluoro[1,1'-biphenyl]-4-ylamineYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Nitro-2′,3′,4′,5′,6′-pentafluorobiphenyl (10 g, 0.0345 mol) was dissolved in absolute ethanol (750 mL) and stirred under a hydrogen atmosphere (1 atm.) over Pd/C (0.3 g) until absorption of hydrogen ceased. The solution was filtered and the solvent was removed. The crude product was purified by column chromatography to give 4-amino-2′,3′,4′,5′,6′-pentafluorobiphenyl as a white powder (8.0 g, 89% yield).

Workup

  1. customuntil absorption of hydrogen
  2. filtrationThe solution was filtered
  3. customthe solvent was removed
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-97dcab5c1bf14561aeaaafe6f4e18302
Source dataset
uspto-grants-2011_03
Patent number
US07902363B2

Reaction notes

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