Category: 27007-53-0

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 2-bromo-5-chlorobenzoate

To a stirred solution of methyl 2-bromo-5-chlorobenzoate (10 g, 40.1 mmol) in 1,4-dioxane (50 mL) cooled to -10 C. was added bis(pinacolato)diboron (12.21 g, 48.1 mmol) and PdCl2(dppf) (1.466 g, 2.004 mmol) followed by potassium acetate (11.80 g, 120 mmol). The mixture was then heated to 90 C. overnight. The reaction mixture was cooled to room temperature, diluted with water (300 mL) and extracted with ethyl acetate (500 mL). The organic layer was separated and dried over sodium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in petroleum ether) to afford methyl 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (11.8 g, 39.8 mmol, 99% yield). LC/MS (ESI) m/e 297.2 [(M+H)+, calcd for C14H19BClO4, 297.1]; LC/MS retention time (Method A1): tR=2.32 min; 1H NMR (400 MHz, CHLOROFORM-d) delta 7.92 (d, J=2.0 Hz, 1H), 7.49 (dd, J=8.0, 2.0 Hz, 1H), 7.45-7.41 (m, 1H), 3.92 (s, 3H), 1.41 (s, 12H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 27007-53-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Nara, Susheel Jethanand; Dzierba, Carolyn Diane; Macor, John E.; Bronson, Joanne J.; Ramkumar, Rajamani; Maishal, Tarun Kumar; Karatholuvhu, Maheswaran Sivasamban; Thangavel, Soodamani; Thiyagarajan, Kamalraj; (77 pag.)US2018/141956; (2018); A1;,
Ester – Wikipedia,
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Reference of 27007-53-0, These common heterocyclic compound, 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, 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 2. methyl 5-chloro-2-cyanobenzoate To a stirred solution of methyl 2-bromo-5-chlorobenzoate (11.5 g, 46 mmol) in degassed DMF (50 mL) was added zinc cyanide (2.82 g, 24.0 mmol) and palladium tetrakis-triphenylphosphine (1.0 g, 0.86 mmol) and the mixture was heated to 90 C. for 18 h. The reaction was partitioned between EtOAc (200 mL) and water (100 mL). The organic phase was concentrated in vacuo and the residue was purified by flash chromatography eluding with a gradient of 10%, 15%, 20% ethyl acetate in hexane yielding methyl 5-chloro-2-cyanobenzoate as a white solid (8.0 g, 88% yield). TLC Rf=0.4 (15% EtOAc-hexanes); HPLC RT=3.13 min (Method A); 1H NMR (CDCl3, 400 MHz) 8.13 ppm (d, 1H, J=1.83 Hz); 8.09 ppm (d, 1H, J=8.24 Hz); 7.29 ppm (dd, 1H, J=8.34, 2.10 Hz); 4.02 ppm (s, 3H). Step. 3 2-aminomethyl-5-chlorobenzyl Alcohol

The synthetic route of 27007-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Williams, Peter D.; Lyle, Terry A.; Morrissette, Matthew M.; Tran, Lekhanh O.; Staas, Donnette D.; US2003/13700; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 27007-53-0

Step B. Methyl 5-chloro-2-cyanobenzoate To a solution of methyl 2-bromo-5-chlorobenzoate (1.15 g, 4.6 mmol) in degassed DMF was added zinc cyanide (282 mg, 2.40 mmol) and palladium tetrakis triphenylphosphine (100 mg, 0.086 mmol) and the reaction is stirred at 90C over night. The reaction was partitioned between ethyl acetate and water. The organic was concentrated in vacuo and purified by flash chromatography eluding a gradient to 10 to 25% ethyl acetate in hexane yielding a white solid (methyl 5-chloro-2-cyanobenzoate). H NMR (CDCl3, 400 MHz): delta 8.13 (d, 1H, J=1.83 Hz); 3.09 (d, 1H, J=8.24 Hz); 7.29 (dd, 1H, J=8.34,2.10 Hz); 4.02(s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 27007-53-0.

Reference:
Patent; Selnick, Harold G.; Barrow, James C.; Nantermet, Philippe G.; Williams, Peter D.; Stauffer, Kenneth J.; Sanderson, Philip E.; Rittle, Kenneth E.; Morrissette, Matthew M.; Wiscount, Catherine M.; Tran, Lekhanh O.; Lyle, Terry A.; Staas, Donnette D.; US2002/119992; (2002); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

27007-53-0, A common compound: 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A solution of 2-bromo-5-chloro-benzoic acid methyl ester Compound 4-2 (5.08 g, 20.4 mmol), the boronate Compound 4-1 (6.00 g, 19.4 mmol), PdCl2dppf-CH2Cl2 (1.06 g, 1.30 mmol) and K2CO3 (8.9 g, 58.21 mmol) in DMF and EtOH (4:1, 90 mL) was prepared in a thick walled tube. The mixture was stirred under argon at rt for 5-10 min and the tube was closed and heated at 90 C. for 5 hrs (4-16 hrs for other examples). The mixture was cooled to rt then filtered thru a pad of Celite, washing with EtOAc. The solvent was evaporated and purified by flash chromatography (gradient elution with 5-50% EtOAc in heptane with 0.1% TEA). The desired product Compound 4-3 was isolated as yellow liquid (4.05 g, 60%). 1H NMR (300 MHz, CDCl3) delta 7.82 (d, J=2.2 Hz, 1H), 7.43 (d of d, J=8.2 and 2.2 Hz, 1H), 7.14 (d, J=8.2 Hz, 1H), 5.51 (br s, 1H), 4.02 (br s, 2H), 3.85 (s, 3H), 3.63 (t, J=5.6 Hz, 2H), 2.30 (br s, 2H), 1.50 (s, 9H); MS (ES+) m/z 374.0 (M+Na).

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, Methyl 2-bromo-5-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ghosh, Shyamali; Kinney, William A.; Lawson, Edward C.; Luci, Diane K.; Maryanoff, Bruce E.; Sommen, Francois Maria; Pan, Yongchun; US2008/39454; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics