Reacción #48070

Ecuación de reacción

3-cyclopropyl-4-fluorophenylamine

caesium iodide

iodine

isoamyl nitrite

→

2-cyclopropyl-1-fluoro-4-iodobenzene

Rendimiento 72.0%

Disolventes

DME

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to RT
2. 2
   Otropartitioned between pentane and sat. NH4Cl solution
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with 5% sodium thiosulfite and brine
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otroto give a residue which
9. 9
   Otrowas purified by flash column chromatography (100% pentane)

Procedimiento

To a solution of 3-cyclopropyl-4-fluorophenylamine (210 mg, 1.39 mmol) in DME (1.5 ml) was added caesium iodide (360 mg, 1.39 mmol), cuprous iodide (82 mg, 0.43 mmol), iodine (176 mg, 0.70 mmol) and isoamyl nitrite (1.11 ml, 8.34 mmol). The reaction mixture was heated to 60° C. for 2 h. The reaction mixture was cooled to RT and partitioned between pentane and sat. NH4Cl solution. The organic layer was separated, washed with 5% sodium thiosulfite and brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (100% pentane) to yield the desired 2-cyclopropyl-1-fluoro-4-iodobenzene (262 mg, 72%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 7.40 (m, 1H), 7.17 (m, 1H), 6.76 (m, 1H), 2.02 (m, 1H), 1.03-0.96 (m, 2H), 0.74-0.68 (m, 2H).

Fuente