3-Fluoro-3'-nitro-1,1'-biphenyl → 3'-Fluorobiphenyl-3-ylamine

HRID 2367674Notes

Reaction equation

HRID 2367674 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1>[Pd].CCO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 572290283-Fluoro-3'-nitro-1,1'-biphenyl

Product 1

HCID 27826793'-Fluorobiphenyl-3-ylamineYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (0.095 g) was added to a solution of 3′-fluoro-3-nitrobiphenyl (L) (0.63 g, 2.88 mmol) in EtOH (20.0 mL). The flask was evacuated and replaced with a hydrogen atmosphere. The solution was stirred at room temperature for 5 h under hydrogen. The catalyst was filtered through a pad of Celite, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography using a 40 g Thomson normal phase silica gel cartridge (100% hexanes→15:85 EtOAc:hexanes) to afford 3′-fluorobiphenyl-3-amine (LI) (0.34 g, 1.81 mmol, 63% yield) as a light yellow oil. 1H NMR (DMSO-d6) δ ppm 7.47-7.44 (m, 1H), 7.40-7.39 (m, 1H), 7.36-7.33 (m, 1H), 7.15-7.14 (m, 1H), 7.10 (t, J=7.7 Hz, 1H), 6.85-6.84 (m, 1H), 6.80-6.79 (m, 1H), 6.60-6.58 (m, 1H), 5.18 (s, 2H); ESIMS found for C12H10FN m/z 188 (M+H).

Workup

  1. customThe flask was evacuated
  2. filtrationThe catalyst was filtered through a pad of Celite
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-480f0774023a42d5848a14141916e0bb
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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