Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing 1-ethyl-3-nitrobenzene

A technology of nitrobenzene and nitrophenyl, which is applied in the field of preparation of 1-ethyl-3-nitrobenzene, can solve the problems of unsuitability for industrial production, high risk of operation, long reaction time, etc., and achieve the goal of preparation process And the purification steps are safe and simple, the product yield is high, and the effect of mild reaction conditions

Active Publication Date: 2019-11-26
安庆睿升医药科技有限公司
View PDF4 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The document Journal of the Chemical Society, 5301-2; 1962 discloses a method of using m-nitroacetophenone as a raw material to obtain 1-ethyl-3-nitrobenzene under the conditions of hydrazine hydrate, potassium hydroxide and 190°C. method, the reaction needs to be carried out under high temperature and high pressure conditions, the operation risk is high, the reaction time is long, the yield is low, and it is not suitable for industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 1-ethyl-3-nitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Preparation of 1-(3-nitrophenyl)ethanol

[0025] Add methanol (50mL) and m-nitroacetophenone (6.6g, 40mmol, 1.0eq) sequentially into a 100mL three-pin bottle, cool to 0°C, add sodium borohydride (2.16g, 60mmol, 1.5eq) in batches, Reacted at room temperature for 1.5 hours, followed by TLC to complete the reaction. Concentrate methanol, add 50mL water to the system and extract twice with ethyl acetate (30mL*2), combine the organic phase, wash twice with saturated brine, dry and concentrate the organic phase with anhydrous sodium sulfate to obtain 1-(3-nitrate phenyl) ethanol 6.5g, yield 97%.

[0026] NMR data: 1H NMR (300MHz, CDCl 3 ):

[0027] δ=1.54(d,3H),5.03(q,1H),7.55-7.50(m,1H),7.74-7.71(m,1H),8.15-8.12(m,1H),8.26-8.25(m ,1H).

[0028] (2) Utilize the 1-(3-nitrophenyl)ethanol obtained in step (1) to prepare 1-(1-iodoethyl)-3-nitrobenzene crude product

[0029] Add dichloromethane (50mL), 1-(3-nitrophenyl)ethanol (3.34g, 20mmol, 1.0eq), imidazole (2.04g, 30...

Embodiment 2

[0035] (1) Preparation of 1-(3-nitrophenyl)ethanol

[0036] Add methanol (50mL) and m-nitroacetophenone (6.6g, 40mmol, 1.0eq) successively in a 100mL three-pin bottle, cool to 0°C, add sodium borohydride (3.1g, 80mmol, 2eq) in batches, and The reaction was carried out at room temperature for 1.5 h, and the reaction was followed by TLC. Concentrate methanol, add 50mL water to the system and extract twice with ethyl acetate (30mL*2), combine the organic phase, wash twice with saturated brine, dry and concentrate the organic phase with anhydrous sodium sulfate to obtain 1-(3-nitrate phenyl) ethanol 6.3g, yield 94.8%.

[0037] NMR data: 1H NMR (300MHz, CDCl 3 ):

[0038] δ=1.54(d,3H),5.03(q,1H),7.55-7.50(m,1H),7.74-7.71(m,1H),8.15-8.12(m,1H),8.26-8.25(m ,1H).

[0039] (2) Utilize the 1-(3-nitrophenyl)ethanol obtained in step (1) to prepare 1-(1-iodoethyl)-3-nitrobenzene crude product

[0040] Add dichloromethane (50mL), 1-(3-nitrophenyl)ethanol (3.34g, 20mmol, 1.0eq), imidaz...

Embodiment 3

[0046] (1) Preparation of 1-(3-nitrophenyl)ethanol

[0047] Add methanol (50mL) and m-nitroacetophenone (6.6g, 40mmol, 1.0eq) sequentially into a 100mL three-pin bottle, cool to 0°C, add sodium borohydride (1.51g, 40mmol, 1.0eq) in batches, The reaction was carried out at room temperature for 3 h, and traced by TLC, a little raw material remained. Concentrate methanol, add 50mL water to the system and extract twice with ethyl acetate (30mL*2), combine the organic phase, wash twice with saturated brine, dry and concentrate the organic phase with anhydrous sodium sulfate to obtain 1-(3-nitrate phenyl) ethanol 5.8g, yield 87.3%.

[0048] NMR data: 1H NMR (300MHz, CDCl 3 ):

[0049] δ=1.54(d,3H),5.03(q,1H),7.55-7.50(m,1H),7.74-7.71(m,1H),8.15-8.12(m,1H),8.26-8.25(m ,1H).

[0050] (2) Utilize the 1-(3-nitrophenyl)ethanol obtained in step (1) to prepare 1-(1-iodoethyl)-3-nitrobenzene crude product

[0051] Add dichloromethane (50mL), 1-(3-nitrophenyl)ethanol (3.34g, 20mmol, 1....

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing 1-ethyl-3-nitrobenzene. The method comprises the following steps: S1. sequentially adding methanol and m-nitroacetophenone into a reaction bottle, cooling the temperature of the reaction bottle to 0 DEG C, adding sodium borohydride in batches, carrying out a reaction at a normal temperature under normal pressure, concentrating methanol, carrying out extracting, merging organic phases, and carrying out concentrating, so as to obtain 1-(3-nitrobenzophenone)ethanol; S2. sequentially adding dichloromethane, the 1-(3-nitrobenzophenone)ethanol, imidazole, triphenyl phosphine and elemental iodine into the reaction bottle, carrying out a reaction at a normal temperature under normal pressure, carrying out extracting, merging organic phases, and carrying out concentrating, so as to obtain crude 1-(1-iodoethyl)-3-nitrobenzene; and S3. dissolving the crude 1-(1-iodoethyl)-3-nitrobenzene in a polar solvent, adding sodium borohydride in batches, carrying out a reaction at a normal temperature under normal pressure, carrying out extracting, merging organic phases, carrying out concentrating, carrying out reduced-pressure distillation, thereby obtaining pure 1-ethyl-3-nitrobenzene. According to the method for preparing the 1-ethyl-3-nitrobenzene, disclosed by the invention, the reaction conditions are mild, a preparation process and purificationsteps are safe and simple, the product yield is high, and thus, industrialization is convenient to achieve.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a preparation method of 1-ethyl-3-nitrobenzene. Background technique [0002] Nitrobenzene derivatives are very commonly used pharmaceutical intermediates in drug synthesis research, and one of the most widely developed and applied varieties. As an important fine chemical raw material, it involves various aspects such as medicine, pesticide, feed and so on. Especially in the last 20 to 30 years, it has been discovered that a large number of nitrobenzene derivatives have become pharmaceutical active intermediates, making the development of p-nitrobenzene derivatives develop in a blowout style. [0003] Document Journal of the Chemical Society, 5301-2; 1962 discloses a kind of using m-nitroacetophenone as raw material, obtains 1-ethyl-3-nitrobenzene under the conditions of hydrazine hydrate, potassium hydroxide and 190°C method, the reaction needs to be carried out und...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/06
CPCC07C201/12C07C205/45C07C205/19C07C205/11C07C205/06
Inventor 李小军檀华东
Owner 安庆睿升医药科技有限公司