Reacción #334376

Ecuación de reacción

5-iodo-1-naphthalenecarboxylic acid methyl ester

trifluoromethyl iodide

→

5-(trifluoromethyl)-1-naphthalenecarboxylic acid methyl ester

Rendimiento 60.4%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   Temperaturacooled to room temperature
3. 3
   FiltraciónThe mixture was filtered
4. 4
   Otroto remove insoluble material
5. 5
   LavadoThe filtrate was washed with 1N aqueous HCl, water and brine
6. 6
   Secadodried (MgSO4)
7. 7
   Concentraciónconcentrated to dryness
8. 8
   OtroThe residue was crystallized from methanol

Procedimiento

A mixture of 5-iodo-1-naphthalenecarboxylic acid methyl ester [8.8 g, 28 mmoles, described by C. Seer and R. School, Justus Leibigs Ann. Chem., 398, 82 (1913)], trifluoromethyl iodide (12 g, 61.2 mmoles), freshly prepared copper powder (5.7 g, prepared according to the procedure of R. Q. Brewster and T. Groening, "Organic Syntheses", Coll. Vol. II, John Wiley and Sons, New York, N.Y., U.S.A., 1948, p. 445) and pyridine (45 ml) was charged into a stainless steel autoclave. The vessel was shaken and heated at 130° C. for 24 hr and cooled to room temperature. The mixture was filtered to remove insoluble material. The filtrate was washed with 1N aqueous HCl, water and brine, dried (MgSO4) and concentrated to dryness. The residue was crystallized from methanol to give 4.3 g of 5-(trifluoromethyl)-1-naphthalenecarboxylic acid methyl ester, NMR (CDCl3) δ 4.0 (s, 3H), 8.0 (m, 6H).

Fuente