Reacción #2195514

Ecuación de reacción

compound

3-Fluoro-2-trimethylsilylphenyl isocyanate

Triethylamine

trichlorosilane

CH2Cl2

isonitrile

NH3

→

3-Fluoro-2-trimethylsilylphenyl isonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 1 h 30 at 0° C.
2. 2
   Otro30 min
3. 3
   Otroat room temperature
4. 4
   Filtraciónfiltered over Celite
5. 5
   Lavadowashed with 5% NaH2PO4
6. 6
   Secadodried (Na2SO4)
7. 7
   OtroThe crude obtained
8. 8
   Otroafter evaporation of the solvent
9. 9
   Otroto afford 1.42 g (66%) of a slighly purple liquid

Procedimiento

A deoxygenation then afforded the expected isonitrile. See Baldwin, J. E. et al., Tetrahedron, 39, 2989 (1983). Triethylamine (4.10 mL, 29.3 mmol) was added slowly at 0° C. to a 2 N solution of trichlorosilane in CH2Cl2 (8.40 mL, 16.8 mmol) followed, 5 min latter, by the compound prepared in Example (3) (2.35 g. 11.2 mmol). After 1 h 30 at 0° C. and 30 min at room temperature, the solution was saturated with NH3, filtered over Celite, washed with 5% NaH2PO4 and dried (Na2SO4). The crude obtained after evaporation of the solvent was then subjected to flash-chromatography (hexanes/AcOEt 95:5) to afford 1.42 g (66%) of a slighly purple liquid: IR (neat, cm−1) 2114, 1598, 1440, 1254, 1237, 1110, 943, 848, 793; 1H NMR (300 MHz, CDCl3) δ 0.45 (d, J=1.8 Hz, 9 H), 7.01 (br t, J=8.3 Hz, 1 H), 7.17 (br d, J=7.7 Hz, 1 H), 7.32 (ddd, J1=J2=8.0 Hz, J3=6.1 Hz, 1 H); 13C NMR (75 MHz, CDCl3) δ 0.1, 116.5 (d, JCF=26 Hz), 124.3, 131.6, 166.8 (d, JCF=243 Hz), 166.9; HRMS (EI) m/z calcd for C10H12FNSi (M+) 193.0723, found 193.0715; LRMS (EI) m/z 193 (M+), 178, 150, 116, 105.

Fuente