2-Fluoro-4-trimethylsilylnitrobenzene → 2-Fluoro-4-(trimethylsilyl)aniline

HRID 2264955Notes

Reaction equation

HRID 2264955 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N+:12]([O-])=O>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([Si:8]([CH3:10])([CH3:9])[CH3:11])[CH:5]=[CH:4][C:3]=1[NH2:12]

Participants

3

Reactant 1

HCID 591401872-Fluoro-4-trimethylsilylnitrobenzene

Product 1

HCID 595965992-Fluoro-4-(trimethylsilyl)anilineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2-fluoro-4-trimethylsilylnitrobenzene (5.45 g, 25.6 mmol) was then dissolved in ethanol (100 mL), transferred to a Parr shaker bottle, flushed with nitrogen, then charged with 10% Pd—C (0.4 g). The reaction mixture was hydrogenated for 1 h on the Parr apparatus (45 psi H2), and then filtered through a plug of Celite. The filter cake was washed with ethanol, and the combined filtrates were concentrated. The resulting residue was purified by flash chromatography (250 mL silica gel, 95:5 hexane-ethyl ether), to afford the title compound as a tan oil (4.31 g, 92%).

Workup

  1. customflushed with nitrogen
  2. additioncharged with 10% Pd—C (0.4 g)
  3. filtrationfiltered through a plug of Celite
  4. washThe filter cake was washed with ethanol
  5. concentrationthe combined filtrates were concentrated
  6. customThe resulting residue was purified by flash chromatography (250 mL silica gel, 95:5 hexane-ethyl ether)

Sources & evidence

ORD record
ord-b7a3bcbda79c45e7ae8d8719a1c94785
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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