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

HRID 79002Notes

Reaction equation

HRID 79002 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>[Pd]>[F:1][C:2]1[CH:3]=[C:4]([Si:11]([CH3:13])([CH3:12])[CH3:14])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

3

Reactant 1

HCID 591401872-Fluoro-4-trimethylsilylnitrobenzene

Product 1

HCID 595965992-Fluoro-4-(trimethylsilyl)anilineYield 99.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A slurry of 10% wt. palladium on carbon (4.0 g) in IMS (25 mL) was added to a solution of (3-fluoro-4-nitro-phenyl)-trimethylsilane (62.0 g, 0.29 mol) in IMS (250 mL) and the reaction mixture flushed with nitrogen five times then hydrogen three times. The reaction mixture was then stirred under 3 bar pressure of hydrogen at room temperature for 4 hours. The reaction mixture was then purged with nitrogen again before filtering through a pad of Celite® with ethyl acetate washings. The filtrate was concentrated under reduced pressure to give the title compound as a light brown oil (53.0 g, quantitative). 1H NMR (CDCl3, 400 MHz) 7.16-7.09 (1H, m), 7.10 (1H, d, J=7.75 Hz), 6.81 (1H, t, J=8.16 Hz), 3.78 (2H, s), 0.26 (9H, s).

Workup

  1. customthe reaction mixture flushed with nitrogen five times
  2. customThe reaction mixture was then purged with nitrogen again
  3. filtrationbefore filtering through a pad of Celite® with ethyl acetate washings
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-58ee18838cb542e5aae75d7756bce5bb
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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