(2,6-Difluoro-4-nitrophenyl)trimethylsilane → 3,5-Difluoro-4-(trimethylsilyl)aniline

HRID 2202208Notes

Reaction equation

HRID 2202208 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[Si:12]([CH3:15])([CH3:14])[CH3:13]>CO.[C].[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([F:11])[C:3]=1[Si:12]([CH3:14])([CH3:13])[CH3:15])[NH2:8]

Participants

4

Reactant 1

HCID 10799521(2,6-Difluoro-4-nitrophenyl)trimethylsilane

Product 1

HCID 1254649723,5-Difluoro-4-(trimethylsilyl)anilineYield 82.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2,6-difluoro-4-nitrophenyl)trimethylsilane (3.5 g, 15.13 mmol) and 10% palladium-carbon (350 mg, 0.16 mmol, 50% wet) in MeOH (70 mL) was stirred at room temperature for 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; ethyl acetate/hexane) to give 3,5-difluoro-4-(trimethylsilyl)aniline (2.50 g, 12.42 mmol, 82%) as a pale-yellow 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; ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bbcc4c23a82a4e9ea841b7797a1b8743
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

Loading…