反応 #48070

反応方程式

3-cyclopropyl-4-fluorophenylamine

caesium iodide

iodine

isoamyl nitrite

→

2-cyclopropyl-1-fluoro-4-iodobenzene

収率 72.0%

溶媒

DME

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to RT
2. 2
   その他partitioned between pentane and sat. NH4Cl solution
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with 5% sodium thiosulfite and brine
5. 5
   乾燥dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他to give a residue which
9. 9
   その他was purified by flash column chromatography (100% pentane)

実験手順

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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