Method for preparing halogenated aryl compounds through oxidation and halogenation
A technology of halogenated aryl and compound, which is applied in the field of fine chemical synthesis to achieve the effects of high yield, good selectivity and mild reaction conditions
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Embodiment 1～6
[0012] Add 2 mmol of catalyst, 5 mmol of anisole, 10 mmol of sodium bromide, 10 mmol of hydrogen peroxide (30% aqueous solution) and 3 mL of water into a round-bottomed flask, and react for 3 hours at room temperature under constant stirring. , extracted twice with 15mL ether, combined the ether extracts, analyzed by gas chromatography, and determined the yield of p-bromoanisole; after gas chromatography analysis, the ether phase was washed with saturated NaHCO 3 The solution and water were washed separately, dried over anhydrous sodium sulfate, distilled off diethyl ether and then distilled under reduced pressure to obtain pure p-bromoanisole. The lower aqueous phase (containing the catalyst) can continue to be recycled. Table 1 shows the results of aqueous phase oxidative bromination of anisole and sodium bromide using different bifunctional imidazolium-based ionic liquids as catalysts.
[0013] Table 1 Aqueous phase oxidative bromination of anisole and sodium bromide wit...
Embodiment 7～15
[0019] Table 2 gives the catalyst 6 Under the action of different halogenated salts or hydrohalic acids and anisole oxidative halogenation reaction results in aqueous phase. 2 mmol catalyst 6 , 5 mmol anisole, 10 mmol halogenated salt (or hydrohalic acid), 10 mmol hydrogen peroxide (30% aqueous solution) and 3 mL water were added to a round bottom flask, and the oxidation was carried out according to the steps and conditions of Examples 1-6 Halogenation reaction.
[0020] Table 2 catalyst 6 The results of the aqueous phase oxidative halogenation reaction of different halogenated salts or hydrohalic acids and anisole a
[0021]
[0022] a 2 mmol catalyst 6 , 5 mmol anisole, 10 mmol halogenated salt (or hydrohalic acid), 10 mmol hydrogen peroxide (30%), 3 mL water, room temperature, reaction time 3 hours.
[0023] b Gas chromatography analysis.
Embodiment 16～30
[0025] Table 3 gives the catalyst 6 The results of the oxidative bromination reaction of hydrobromic acid and anisole in different ionic liquids. 0.5 mmol catalyst 6 , 5 mmol anisole, 5 mmol hydrobromic acid, 7.5 mmol hydrogen peroxide (30% aqueous solution) and 3 mL of different ionic liquids were added to a round bottom flask, and the oxidative bromination reaction was carried out according to the steps and conditions of Examples 1-6 .
[0026] table 3 catalyst 6 Oxidative Bromination Results of Hydrobromic Acid and Anisole in Different Ionic Liquids a
[0027]
[0028] a 0.5 mmol catalyst 6 , 5 mmol anisole, 5 mmol hydrobromic acid, 7.5 mmol hydrogen peroxide (30%), 3 mL ionic liquid, room temperature, reaction time 3 hours.
[0029] b Bmim=1-methyl-3-butylimidazolium quaternary ammonium cation; Bpy=N-butylpyridinium quaternary ammonium cation.
[0030] c OAc=acetate, OTs=p-toluenesulfonate, NTf 2 = trifluoromethylsulfonimide anion.
[0031] d Gas chro...
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