Réaction #48070

Équation de réaction

3-cyclopropyl-4-fluorophenylamine

caesium iodide

iodine

isoamyl nitrite

→

2-cyclopropyl-1-fluoro-4-iodobenzene

Rendement 72.0%

Solvants

DME

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to RT
2. 2
   Autrepartitioned between pentane and sat. NH4Cl solution
3. 3
   AutreThe organic layer was separated
4. 4
   Lavagewashed with 5% sodium thiosulfite and brine
5. 5
   Séchagedried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   Autreto give a residue which
9. 9
   Autrewas purified by flash column chromatography (100% pentane)

Mode opératoire

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).

Source