A kind of preparation method of 1-bromoalkyne and 1-iodoalkyne

Abstract

The invention discloses a preparation method of 1-bromoalkyne and 1-iodoalkyne. The preparation method comprises the following steps that terminal alkyne is adopted as a raw material, a chloramine salt and an iodine salt or a bromine salt is adopted as a halogenation system, and reaction is carried out in a solvent to synthesize a series of 1-bromoalkyne and 1-iodoalkyne type compounds. In the formula shown in the description, R in terminal alkyne is selected from chain-like alkyne, ring-shaped alkyne, olefin, ester group, cyanogroup, substituted phenyl group and heterocyclic arene; the chloramine salt is selected from one of chloramine B, chloramine T or o-chloramine T; the iodine salt is selected from one of sodium iodide, potassium iodide, ammonium iodide, lithium iodide or tetrabutylammonium iodide; the bromine salt is selected from one of sodium bromide, potassium bromide, lithium bromide, magnesium bromide, ammonium bromide or tetrabutylammonium bromide; the solvent is selected from one or is mixed by two of water, benzene, methylbenzene, 1, 4-dioxane, ethyl acetate, dimethyl sulfoxide, methanol, tetrahydrofuran, alcohol, isopropyl alcohol, N, N-dimethyl formamide, n-pentane,dichloromethane, petroleum ether, methyl tert-butyl ether, chloroform, n-hexane, carbon tetrachloride, n-butyl alcohol, 1,2-dichloroethane or acetonitrile. The preparation method disclosed by the invention has the beneficial effect that the application is wide.

Description

technical field

[0001] The invention relates to a preparation method of 1-bromoalkyne and 1-iodoalkyne, belonging to the field of organic synthesis chemistry. Background technique

[0002] Halogen-containing compounds widely exist in organic synthesis intermediates, active natural products, drugs, pesticides and material molecules. Among them, 1-bromoalkynes and 1-iodoalkynes have attracted the attention of chemists, because they are not only used as synthetic building blocks in organic chemistry, but also as important synthetic precursors in materials and polymer chemistry. Wide range of uses. For the synthesis of 1-bromoalkynes and 1-iodoalkynes, the most common strategy is the direct C–H oxidative halogenation of terminal alkynes. The synthesis reports of 1-iodoalkyne include: strong base / iodine simple substance, ionic liquid, metal reagent, electrode oxidation method, N-iodo-morphonine, KI or Me 3 SI / PhI(OAc) 2 , Hypervalent iodonium salt and iodosuccinimide system. ...

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