Category: 20330-90-9

Application of 20330-90-9,Some common heterocyclic compound, 20330-90-9, name is Dimethyl 5-chloroisophthalate, molecular formula is C10H9ClO4, 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.

5-Chloro isophthalic acid monomethyl ester:; To a solution of 4.92 g (21.5 mmol) dimethyl 5-chloro isophthalat in a mixture of 30 ml methanol and 20 ml tetrahydrofuran are added 1.09 g (19.4 mmol) potassium hydroxide in small portions. The mixture is heated to reflux for 6 hours and 2 days at room temperature. The solvents are removed at reduced pressure. The residue is dissolved in a mixture of water and dichloromethane. The organic layer is acidified with 2M hydrochloric acid to pH 1. The precipitate is filtered off and dried at 40 0C at reduced pressure. 3.08 g of the title compound are obtained as a colorless solid (M-H+ = 213.0).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 5-chloroisophthalate, its application will become more common.

Reference:
Patent; ALTANA PHARMA AG; WO2006/79645; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 20330-90-9, A common heterocyclic compound, 20330-90-9, name is Dimethyl 5-chloroisophthalate, molecular formula is C10H9ClO4, 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.

Step 1. Methyl 3-chloro-5-(hydroxymethyl)benzoate To a solution of dimethyl 5-chloroisophthalate (10.0 g, 43.7 mmol, Astatech) in methanol (50 mL) and methylene chloride (50 mL) at 0 C. was added sodium borohydride (5.5 g, 140 mmol, Aldrich). The reaction was allowed to gradually reach room temperature and stir for 1 hour. Additional portions of sodium borohydride (0.50 g, 13 mmol) were added at 2 hours and 3 hours. The reaction mixture was cooled to 0 C. and the reaction was quenched with water. The layers were separated and the aqueous layer was extracted with three portions of DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-25% EtOAc in hexanes. Yield: (4.51 g, 51%). 1H NMR (400 MHz, CDCl3) delta 7.92-7.90 (m, 1H), 7.90-7.88 (m, 1H), 7.57-7.55 (m, 1H), 4.73 (s, 2H), 3.92 (s, 3H); LCMS (M+H)+: 201.1203.1.

The synthetic route of 20330-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; US2015/175604; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 20330-90-9 as follows. Computed Properties of C10H9ClO4

A mixture of dimethyl 5-chloroisophthalate (6.84 g, 30 mmol), in methanol (150 mL) was treated with 1M sodium hydroxide (27 mL, 27 mmol) and the reaction stirred at room temperature for 16 hours. The mixture was concentrated under vacuum and the resulting residue was dissolved in water. The mixture was extracted with ethyl acetate three times. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to afford 3-chloro-5-(methoxycarbonyl)benzoic acid (4.8 g, 75%).

According to the analysis of related databases, 20330-90-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gerritz, Samuel; Shi, Shuhao; Zhu, Shirong; US2006/287287; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 20330-90-9, name is Dimethyl 5-chloroisophthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Dimethyl 5-chloroisophthalate

To a solution of 1,3-dimethyl 5-chlorobenzene-l ,3-dicarboxylate (4.00 g, 17.5 mmol) in dioxane (50 mL) and water (50 mL) was added NaOH (700 mg, 17.5 mmol). The resulting suspension was stirred vigorously at 40C for 2 hrs and then for a further 16 hrs at room temperature. The reaction mixture was evaporated to dryness, re-dissolved in water (-200 mL) and acidified to pH 3 using 1M HCl. The resulting white precipitate was sonicated for 2 mins and filtered. The white solid was washed further with water and then dried in a vacuum oven overnight. This afforded a white solid (3.6 g) which was a mixture of 3 products including 3-chloro-5-(methoxycarbonyl)benzoic acid. This solid was dissolved in DMF (150 mL) at 0C and diethylamine (2.56 g, 0.03 mol), DIPEA (6.09 ml, 0.03 mol) and HATU (6.64 g, 0.02 mol) were added. The reaction mixture was then stirred at room temperature for 6 hrs then evaporated to dryness, re- dissolved in EtOAc (200 mL) and washed with water (3 x 200 mL) and brine (2 X200 mL). The combined organics were then dried over MgSC>4 and evaporated to dryness to afford the crude product. This was purified by silica chromatography (Biotage: lOOg SNAP cartridge) eluting with 0-80% EtOAc in heptane to afford the title compound as a colourless oil (880 mg (28%); H NMR (500 MHz, CDC13) 5 1.13 (br. s, 3H), 1.26 (t, 3H), 3.24 (br.s, 2H), 3.54 (br. s, 2H), 3.93 (s, 3H),7.55 (m, 1H), 7.92 (m, 1H), 8.04 (m, 1H).

The synthetic route of 20330-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics