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A kind of method that prepares alkyl phosphonate by peroxide

A technology of alkyl phosphonyl compounds and peroxides, which is applied in the field of preparation of organic compounds, can solve problems such as cumbersome operation, harsh reaction conditions, and large pollution, and achieve simple reaction operation and post-treatment process, mild reaction conditions, and high reaction efficiency. short time effect

Active Publication Date: 2021-12-10
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The disclosed preparation method of alkylarylphosphine (2) has harsh reaction conditions, active raw material diphenylphosphine chloride, difficult storage, cumbersome operation and low yield
The disclosed alkyl phosphonates are mainly synthesized by the reaction of halogenated hydrocarbons and trialkyl phosphite, which requires high temperature and relatively large pollution

Method used

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  • A kind of method that prepares alkyl phosphonate by peroxide
  • A kind of method that prepares alkyl phosphonate by peroxide
  • A kind of method that prepares alkyl phosphonate by peroxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: Synthesis of n-undecyl-bis(4-methylphenyl)phosphine oxide

[0052] Using lauroyl peroxide (abbreviated as LPO, CAS No.: 105-74-8) and bis(4-methylphenyl)phosphine oxide as raw materials, the reaction steps are as follows:

[0053] To LPO (199 mg, 0.5 mmol) was added cuprous chloride (9.9 mg, 0.1 mmol), 4,4'-dimethoxy-2,2'-bipyridine (10.8 mg, 0.05 mmol), acetone ( 1 mL) and bis(4-methylphenyl)phosphine oxide (57.5 mg, 0.25 mmol), the reaction was stirred at room temperature and monitored by TLC until the end of the reaction;

[0054] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: acetone=4:1) to obtain the target product n-undecyl-bis(4-methylphenyl)phosphine oxide (yield 75%); The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.60 (t, J = 8.1 Hz, 4H), 7.26 (d, J = 7.7 Hz, 4H), 2.38 (s, 6H), 2.21 (d, J = 6.1 Hz, 2H), 1.60 (s, 2H), 1.41-1.32 (m, 2H), 1.31-1.17...

Embodiment 2

[0055] Example 2: Synthesis of n-undecyl-bis(4-chlorophenyl)phosphine oxide

[0056] Using LPO and bis(4-chlorophenyl)phosphine oxide as raw materials, the reaction steps are as follows:

[0057] To LPO (199 mg, 0.5 mmol) was added cuprous bromide (14.3 mg, 0.1 mmol), 1,10-phenanthroline (18.2 mg, 0.1 mmol), ethanol (1 mL) and bis(4-chlorobenzene base) phosphine oxide (67.8 mg, 0.25 mmol), 60 o C stirring reaction, TLC monitors to the end of reaction;

[0058] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: acetone = 4:1) to obtain the target product (yield 83%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.6-7.59 (m, 4H), 7.43(d, J = 6.9 Hz, 4H), 2.26-2.15 (m, 2H), 1.64-1.51 (m, 2H), 1.40-1.31 (m,2H), 1.28-1.16 (m, 14H), 0.85 (t, J = 6.9 Hz, 3H).

Embodiment 3

[0059] Example 3: Synthesis of n-undecyl-bis(thienyl)phosphine oxide

[0060] With LPO and dithienyl phosphine oxide as raw materials, the reaction steps are as follows:

[0061] To LPO (199 mg, 0.5 mmol) was added cuprous cyanide (5.4 mg, 0.06 mmol), 2,9-dimethyl-1,10-phenanthroline (10.4 mg, 0.05 mmol), ethyl acetate ( 1 mL) and dithienylphosphine oxide (53.6 mg, 0.25mmol), 40 o C stirring reaction, TLC monitors to the end of reaction;

[0062] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: acetone = 4:1) to obtain the target product (yield 80%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 7.69 (t, J = 4.1 Hz,2H), 7.58 (dd, J = 6.9, 3.3 Hz, 2H), 7.20-7.15 (m, 2H), 2.31-2.21 (m, 2H),1.74-1.59 (m, 2H), 1.37 (dd, J = 14.1, 7.0 Hz, 2H), 1.31-1.16 (m, 14H), 0.85 (t, J = 6.9 Hz, 3H).

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Abstract

The invention discloses a method for preparing alkyl phosphonate from peroxide. The present invention uses acyl peroxide as the starting material, and the raw materials are easy to obtain and have many types; the products obtained by the method of the present invention are of various types and have wide applications, and some products can be obtained through simple reduction to important phosphorus ligands and key intermediates of drugs . In addition, the method of the invention avoids the use of highly toxic phosphine reagents, has mild reaction conditions, simple operation, high yield of the target product, low pollution, simple reaction operation and post-treatment process, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a method and application of an alkyl phosphonate prepared from a peroxide. Background technique [0002] Alkylarylphosphine oxides (1) are important building blocks for the synthesis of flame retardant materials and have important applications in the flame retardant industry (References: Li Chen, Chao Ruan, Rong Yang and Yu-Zhong Wang. Polym. . 2014, 5 , 3737–3749. Albrecht Granzow. Acc. Chem. Res 1978, 11 , 177-183.); meanwhile, alkylarylphosphine oxide (1) can be easily reduced to alkylarylphosphine (2), the reaction formula is as follows. [0003] [0004] 2, as a phosphorus ligand, is widely used in the fields of organometallic chemistry, coordination chemistry and asymmetric chemistry (reference: Jun-An Ma. Chem. Soc. Rev . 2006, 35 , 630–636). [0005] Alkyl phosphonates have various physiological activities and are widely use...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/53C07F9/6553C07F9/40C07F9/50C07F9/38C07F9/30
CPCC07F9/5325C07F9/655345C07F9/4075C07F9/5022C07F9/3882C07F9/5333C07F9/306
Inventor 邹建平李成坤陶泽坤
Owner SUZHOU UNIV
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