Hydrochloric Acid → HCID 131725738, compound

Participants

Reaction Conditions

Reaction Steps

4-Iodoaniline (8.8 g, 40 mmol) was suspended in a mixture of conc. HCl (20 mL) and H2O (50 mL) and cooled to 0° C. A solution of NaNO2 (3.3 g, 48 mmol) in H2O (10 mL) was added dropwise with stirring while the temperature was carefully maintained at 0–5° C. After the addition was completed, the mixture was stirred for 30 min at 0° C. The resulting diazonium salt solution was then added slowly to a solution of ferrocene (3.7 g, 20 mmol) in toluene (100 mL) at 0° C. An instantaneous evolution of gas was observed. After complete addition, the reaction mixture was stirred at 0° C. for 1 h. Then the mixture was warmed to rt and stirring was continued for 16 h. The layers were separated and the aqueous layer was extracted with toluene (3×100 mL). The combined organic layers were washed with satd aq NaHCO3 (3×100 mL), brine (3×100 mL), dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:2) to afford 4.2 g (55%) of an orange solid: mp 119–121° C.; 1H NMR δ 4.02 (s, 5H), 4.33 (t, J=1.5 Hz, 2H), 4.61 (t, J=1.5 Hz, 2H), 7.20,7.58 (AA′BB′, J=7.8 Hz, 4H); 13C NMR δ 66.4, 69.2, 69.7, 84.1, 90.5, 127.9, 137.3, 139.2; FAB-MS obsd 387.9420 calcd exact mass 387.9411 (C16H13FeI).

Provenance & Evidence