(2-Fluoro-4-nitrophenyl)trimethylsilane → 3-Fluoro-4-(trimethylsilyl)aniline

HRID 2202304Notes

Reaction equation

HRID 2202304 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[Si:11]([CH3:14])([CH3:13])[CH3:12]>CO.[C].[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[Si:11]([CH3:14])([CH3:13])[CH3:12])[NH2:8]

Participants

4

Reactant 1

HCID 125465550(2-Fluoro-4-nitrophenyl)trimethylsilane

Product 1

HCID 916190603-Fluoro-4-(trimethylsilyl)anilineYield 68.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2-fluoro-4-nitrophenyl)trimethylsilane (3.22 g, 15.10 mmol) and 10% palladium-carbon (1.0 g, 0.47 mmol, 50%, wet) in MeOH (65 mL) was stirred at room temperature for 3.5 hr under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 2→15% MeOH/ethyl acetate) to give 3-fluoro-4-(trimethylsilyl)aniline (1.89 g, 10.31 mmol, 68.3%) as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 2→15% MeOH/ethyl acetate)

Sources & evidence

ORD record
ord-3313c17805344abba116e8b3960edbcd
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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