458-03-7 Archives - Ethers-buliding-blocks

Share a compound : C8H9FO

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Ethoxy-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Electric Literature of 458-03-7, The chemical industry reduces the impact on the environment during synthesis 458-03-7, name is 1-Ethoxy-3-fluorobenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 92 To 29.8 g of 2,3-dichloro-4-methoxybenzoyl chloride in 150 ml of 1,2-dichloroethane, 16.3 g of m-fluorophenetole is added. The solution is chilled to 5 C. as 16.5 g of aluminum chloride is added slowly. After 2 hr, the reaction mixture is worked up with water and diethyl ether to give a mixture of 2,3-dichloro-4′-ethoxy-2′-fluoro-4-methoxybenzophenone and 2,3-dichloro-2′-ethoxy-4′-fluoro-4-methoxybenzophenone. The mixture is separated by preparative high pressure liquid chromatography (10% ethyl acetate/hexane 250 ml/min) to give 2,3-dichloro-4′-ethoxy-2′-fluoro-4-methoxybenzophenone, mp 94-96 C. Analysis: Calculated for C16 H13 Cl2 FO3: 55.99%C; 3.82%H. Found: 55.86%C; 3.81%H.

Reference:
Patent; Hoechst-Roussel Pharmaceuticals, Inc.; US4673746; (1987); A;,
Ether – Wikipedia,
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Sources of common compounds: 1-Ethoxy-3-fluorobenzene

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 458-03-7, name is 1-Ethoxy-3-fluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Ethoxy-3-fluorobenzene

First Step In a reaction vessel under a nitrogen atmosphere, 14.5 g (103 mmol) of 1-ethoxy-3-fluorobenzene (No. 1) was dissolved into 150 mL of THF. At a temperature of -70 C. or lower, 100 mL (102 mmol) of s-butyllithium (1.02 M cyclohexane solution) was added dropwise to the solution, and the resultant mixture was stirred for 1 hour, and then a THF (50 mL) solution of 14.0 mL (110 mmol) of trimethylsilyl chloride was added dropwise thereto. The resultant mixture was stirred for 1 hour, and then the reaction mixture was poured into 300 mL of aqueous solution of ammonium chloride subjected to ice-cooling, and then liquids were separated. An aqueous layer was extracted with 100 mL of hexane twice, organic layers were combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then a solvent was evaporated under reduced pressure. A residue was treated on silica gel column chromatography (silica gel:400 g, eluate:heptane), and then subjected to vacuum distillation (136 C., 50 mmHg), and thus 14.1 g (66.2 mmol, yield 64 mol %) of 1-ethoxy-3-fluoro-trimethylsilylbenzene (No. 2) was obtained.

Analyzing the synthesis route of 458-03-7

Reference of 458-03-7, A common heterocyclic compound, 458-03-7, name is 1-Ethoxy-3-fluorobenzene, molecular formula is C8H9FO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

2- (3-Ethoxy-phenyl)-2-methyl-propionitrile was prepared using a procedure adapted from literature (Organic Syntheses, Vol. 79, pp. 209-215). To a solution of 1-ethoxy-3-fluoro benzene (3.0 g, 19.4 mmol) in 25 mL of toluene was added solid potassium bis (trimethylsilyl)amide (5.84g, 29.2 mmol, 1.5 eq) followed by isobutyronitrile (7.08 mL, 77.8 mmol, 4 eq). The reaction mixture was stirred at 100 C for 12 hr. It was diluted with 75 mL of ethyl acetate and 75 mL of IN aqueous hydrochloric acid. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water (1 x 50 mL), brine (1 x 50 mL), and dried over anhydrous magnesium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo. The residue was dissolved in 5 mL of methylene chloride and applied to a 40 g silica gel cartridge. The product was eluted using a gradient of ethyl acetate in hexanes to yield 2.96 g (15.6mmol, 80%) of pure 2-(3-ethoxy- phenyl) -2-methyl-propionitrile. LR-MS: 190.12 [(M+H)+] 2- (3-Ethoxy-phenyl)-2-methyl-propionitrile (2.96 grams, 15.65 mmol) was dissolved in a freshly prepared acetic acid solution of iodine monochloride (20 mL of a 1.54 M iodine monochloride solution in acetic acid, 30.8 mmol). The reaction was slightly exothermic. The reaction mixture was allowed to stand at room temperature for 3 d. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 10% sodium carbonate (1x), brine (1x), and dried (anhydrous magnesium sulfate). The solids were filtered off, and the filtrate was concentrated to dryness. The residue was purified by flash chromatography (110 g of silica gel, eluting with a gradient of ethyl acetate in hexanes) to give 2- (3-ethoxy-4-iodo-phenyl)-2-methyl-propionitrile g, 51%). LR-MS: 316.21 [(M+H)+] Nitrogen gas was bubbled through a solution of (3-ethoxy-4-iodo-phenyl)-2-methyl- propionitrile (2.53 grams, 8 mmol) and diisopropylethylamine (2.09 mL, 12 mmol) in methanol (10 mL). Using a balloon filled with carbon monoxide gas (CO) and equipped with a needle, CO was bubbled through the mixture until it was saturated. Palladium (II) acetate (100 mg) was added, and the mixture was stirred under an atmosphere of CO at 60 C for 6 d. The reaction mixture was filtered and concentrated. The residue was partitioned between methylene chloride and 1.0M hydrochloric acid. The organic layer was dried (anhydrous magnesium sulfate), filtered. The residue was purified by flash chromatography (120 g of silica gel, eluting with a gradient of ethyl acetate in hexanes) to give methyl 4-(cyano-dimethylmethyl)-2-ethoxy- benzoate (1.09 g, 55%). LR-MS: 248.19 [(M+H)@]

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; WO2005/110996; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Continuously updated synthesis method about 1-Ethoxy-3-fluorobenzene

Adding a certain compound to certain chemical reactions, such as: 458-03-7, name is 1-Ethoxy-3-fluorobenzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 458-03-7, 458-03-7

First Step In a reaction vessel under a nitrogen atmosphere, 1.94 g (7.2 mmol) of 2-(4-ethoxy-2-fluoro-3-trimethylsilylphenyl)acetate (No. 5) obtained in the fourth step in Example 1 was dissolved into 25 mL of THF. The solution was cooled to 0 C., 8.6 mL (14.4 mmol) of s-butyllithium (1.67 M n-hexane solution) was added dropwise thereto, and subsequently the reaction mixture was heated to room temperature and stirred for 30 minutes. Subsequently, the resultant reaction mixture was cooled to -70 C., a THF (15 mL) solution of 1.9 g (7.2 mmol) of 2-(trans-4-propyl-cyclohexyl)cyclohexyl-oxetane (No. 26) obtained according to a method described in JP 2000-8040 A, and subsequently a THF (3 mL) solution of 1.08 mL (8.6 mmol) of boron trifluoride-diethyl ether complex were added dropwise thereto.

Reference:
Patent; JNC CORPORATION; JNC PETROCHEMICAL CORPORATION; Goto, Mayumi; Fujimori, Sayaka; US9102871; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem