반응 #48070

반응 방정식

3-cyclopropyl-4-fluorophenylamine

caesium iodide

iodine

isoamyl nitrite

→

2-cyclopropyl-1-fluoro-4-iodobenzene

수율 72.0%

용매

DME

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to RT
2. 2
   기타partitioned between pentane and sat. NH4Cl solution
3. 3
   기타The organic layer was separated
4. 4
   세척washed with 5% sodium thiosulfite and brine
5. 5
   건조dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타to give a residue which
9. 9
   기타was purified by flash column chromatography (100% pentane)

실험 절차

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).

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