ChemicalBook CAS DataBase List 4-Cyclopropyl-2-fluoro-1-iodobenzene

4-Cyclopropyl-2-fluoro-1-iodobenzene synthesis

5synthesis methods

Product Name:4-Cyclopropyl-2-fluoro-1-iodobenzene
CAS Number:1030383-32-4
Molecular formula:C9H8FI
Molecular Weight:262.07

893739-89-4
39 suppliers
inquiry

1030383-32-4
12 suppliers
inquiry

Yield:1030383-32-4 71.28%

Reaction Conditions:

Stage #1: 4-cyclopropyl-2-fluoroanilinewith sulfuric acid;potassium iodide;sodium nitrite in dichloromethane;water at 0; for 0.0833333 h;
Stage #2: with potassium iodide in dichloromethane;water at 60; for 3 h;

Steps:

52.4

Step 4: Preparation of 4-cyclopropyl-2-fluoro-1-iodobenzene To a stirred mixture of 4-cyclopropyl-2-fluoroaniline (1.63 g, 10.78 mmol) in water (20 mL) at 0° C. was added concentrated sulfuric acid (8.6 mL, 15.0 eq.) dropwise, while keeping the temperature constant at 0° C. A solution of sodium nitrite (781.0 mg, 11.32 mmol, 1.05 eq.) in water (2.7 mL) was added and stirred for 5 minutes. This resulting reaction mixture was then added to a solution of potassium iodide (3.76 g, 22.64 mmol, 2.1 eq.) in water (9.7 mL), and the reaction mixture was stirred at 60° C. for 3 h. DCM (400 mL) was added to the cooled reaction. The biphasic layers were separated, and the aqueous layer was extracted with DCM (2*150 mL). The combined organic layers were washed with saturated aqueous Na₂S₂O₄, water, and brine, dried over Na₂SO₄, filtered, and concentrated under reduced pressure. The crude residue was purified via flash column chromatography eluted with 100% heptane to give 2.01 g (71.28%) of 4-cyclopropyl-2-fluoro-1-iodobenzene as a clear oil. ¹H NMR (400 MHz, CDCl₃) δ 7.57 (dd, J=8.0, 6.9 Hz, 1H), 6.76 (dd, J=9.4, 1.9 Hz, 1H), 6.64 (dd, J=8.2, 1.9 Hz, 1H), 1.94-1.77 (m, 1H), 1.09-0.95 (m, 2H), 0.79-0.56 (m, 2H).

References:

US2011/251176,2011,A1 Location in patent:Page/Page column 114

893739-89-4
39 suppliers
inquiry

96042-30-7 Synthesis