Iodine → 2-Cyclopropyl-1-fluoro-4-iodobenzene

Temperature

60 °C

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).

1. temperatureThe reaction mixture was cooled to RT
2. custompartitioned between pentane and sat. NH4Cl solution
3. customThe organic layer was separated
4. washwashed with 5% sodium thiosulfite and brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a residue which
9. customwas purified by flash column chromatography (100% pentane)

ORD record

ord-27835b63b9e04a92b1eee076253f85c2

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745477B2