تفاعل #48070

معادلة التفاعل

3-cyclopropyl-4-fluorophenylamine

caesium iodide

iodine

isoamyl nitrite

→

2-cyclopropyl-1-fluoro-4-iodobenzene

المردود 72.0%

المذيبات

DME

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to RT
2. 2
   أخرىpartitioned between pentane and sat. NH4Cl solution
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with 5% sodium thiosulfite and brine
5. 5
   تجفيفdried (MgSO4)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىto give a residue which
9. 9
   أخرىwas purified by flash column chromatography (100% pentane)

الإجراء التجريبي

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).

المصدر