2-fluoro-4-trimethylsilylaniline synthesis

5synthesis methods

Product Name:2-fluoro-4-trimethylsilylaniline
CAS Number:955372-99-3
Molecular formula:C9H14FNSi
Molecular Weight:183.3

Benzene, 2-fluoro-1-nitro-4-(trimethylsilyl)-

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Yield:955372-99-3 100%

Reaction Conditions:

with hydrogen;palladium on activated carbon in methylated spirits at 20; under 2250.23 Torr; for 4 h;Product distribution / selectivity;

Steps:

A.2

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.O g, quantitative). ¹H NMR (CDCl₃) 7.16-7.09 (IH, m), 7.10 (1 H, d, J = 7.75 Hz), 6.81 (1 H, t, J = 8.16 Hz), 3.78 (2 H, s), 0.26 (9 H, s).

References:

WO2009/85983,2009,A1 Location in patent:Page/Page column 51-52