1-(1,1-Difluoroethyl)-3-nitrobenzene → 3-(1,1-Difluoroethyl)aniline

HRID 1640139Notes

Reaction equation

HRID 1640139 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)([F:4])[CH3:3]>CC(O)=O.CCOC(C)=O.[Zn]>[F:1][C:2]([C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)([F:4])[CH3:3]

Participants

5

Reactant 1

HCID 108778561-(1,1-Difluoroethyl)-3-nitrobenzene

Product 1

HCID 234450923-(1,1-Difluoroethyl)aniline

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(1,1-difluoroethyl)-3-nitrobenzene (2.75 g, 14.7 mmol) in AcOH (30 mL) was added zinc (10.0 g, 153 mmol). The reaction mixture was allowed to stir at rt overnight. The mixture was diluted with EtOAc (40 mL) and filtered through Celite. The filtrate was concentrated. The residue was diluted with DCM (20 mL), washed with saturated NaHCO3 (20 mL) and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(1,1-difluoroethyl)benzenamine as light brown oil. 1H NMR (300 MHz, DMSO) δ 7.21 (dd, 1H), 6.89 (s, 1H), 6.80 (d, 1H), 6.79 (d, 1H), 186 (t, 3H); LCMS: ES+ 158.1.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. additionThe residue was diluted with DCM (20 mL)
  4. washwashed with saturated NaHCO3 (20 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3c60a7b919394ee2ae5c20f9e6d43e43
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

Loading…