A kind of halogenation method of aromatic compound
A technology of aromatic compounds and halogenated reagents, which is applied in the field of organic synthesis, can solve the problems of few synthetic methods, the inability to industrialize the production of halogenated phenols, and the low utilization rate of bromine atoms, and achieve wide sources of reaction substrates, cheap and easy-to-obtain catalysts, Effect of excellent substrate suitability
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Embodiment 1
[0031] Example 1: Self-made catalyst Fe(OMs) in our laboratory 3 (1).
[0032] Under an air atmosphere, iron hydroxide (0.19 mmol) was dissolved in 5 mL of water, then 5 mL of an aqueous solution dissolved in methanesulfonic acid (0.19 mmol) was slowly added dropwise, and stirred at room temperature for 12 hours; The filtrate was concentrated under negative pressure to obtain a gray solid with a yield of 90%.
[0033] 1. Preparation of ortho-chlorinated products of aromatic amines.
Embodiment 2
[0034] Example 2: Preparation of 2-chloro-N-methylaniline (2) from N-methylaniline.
[0035]
[0036] Under air atmosphere, iron p-toluenesulfonate (5 mol%, 5.7 mg), N-methylaniline (0.2 mmol, 21.4 mg), trichloroisocyanuric acid (0.07 mmol, 16.3 mg) and a magnetic stirrer Add to 35mL glass pressure-resistant tube. Then, toluene (4 mL) was added, and the reaction tube was reacted at 90°C for 12 hours. After the reaction was completed, the reaction system was cooled to room temperature, the reaction vessel was opened at room temperature, 10 mL of water was added; extracted with 30 mL of dichloromethane, the organic phase was collected, dried with anhydrous sodium sulfate, and the organic layer was purified by column chromatography, The pure yield of the ortho-position target product is 78%, and the gas-phase selectivity of ortho-position and para-position is o:p=91:9. (The descriptions of imide by-products and para-products are omitted in the reaction formulas of the follow...
Embodiment 3
[0038] Example 3: N-Ethylaniline Preparation of 2-chloro-N-ethylaniline (3).
[0039]
[0040] Under air atmosphere, scandium trifluoromethanesulfonate (5 mol%, 4.9 mg), N-ethylaniline (0.2 mmol, 24.2 mg), trichloroisocyanuric acid (0.07 mmol, 16.3 mg) and a magnetic stirrer were added into a 35mL glass pressure-resistant tube. Then, toluene (4 mL) was added, and the reaction tube was reacted at 90°C for 12 hours. After the reaction was completed, the reaction system was cooled to room temperature, the reaction vessel was opened at room temperature, 10 mL of water was added; extracted with 30 mL of dichloromethane, the organic phase was collected, dried with anhydrous sodium sulfate, and the organic layer was purified by column chromatography, The pure product was obtained in 77% yield, and the gas-phase selectivity between ortho and para positions was o:p=84:16.
[0041] 1 H NMR (400MHz, CDCl 3 )δ7.26-7.24(m,1H),7.16-7.09(m,1H),6.67-6.54(m,2H),4.19(br,1H),3.23-3.18(m,2...
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