Author: Jessica.F

Electric Literature of 452-63-1, The chemical industry reduces the impact on the environment during synthesis 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

4-Fluoro-2-methylphenylacetic acid To a 2L flask containing 2-dicyclohexylphosphino-2′-(N, N- dimethylamino)biphenyl.(3.76g) and Pd(OAc)2 (1.02g) were added 396 mL of IN LHMDS in hexanes, then 400 mL of toluene under N2. The solution was cooled to -10 0C and tButyl acetate (49 mL was added. The solution was stirred at -10 0C for 10 min and was added 2-bromo-5-fiuoro toluene. The mixture was heated at 80 0C for 15 min and was washed with NH4Cl and NaCl, dried with Na2SO4, filtered and concentrated. The crude was purified by flash chromatorghy with EtOAc/hexanes = 1 :30 to give tert-bvAyl (4-fluoro-2-methylphenyl)acetate (21.85g).The pure ester was dissolved in 60 ml Of CH2Cl2 was added 6 drops of anisole and 60 ml OfCFaCO2H and the solution was atirred at rt for 16hr. Upon removal of volatiles, the residue was dried three times by dissolving in toluene to afford 20.02 g of the title compound. 1H- NMR (CDCI3): delta 2.35 (s, 3H), 3.67 (s, 2H), 6.92-6.95 (m, 2H), 7.19 (d of d, IH, J = 8.2, 5.7 Hz) ppm.

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-Bromo-4-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/75528; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2,4,5-trifluorobenzene

A 1-L, one-necked, round-bottom flask, equipped with a Tefloncoatedmagnetic stirring bar, was removed from a drying oven at150 C, sealed while hot with a rubber septum, purged with dry N2,and cooled to r.t. (22 C). 1-Bromo-2,4,5-trifluorobenzene (1; 50.0mL, 90.0 g, 0.427 mol; Oakwood Products) and anhydrous THF(400 mL) were added from a syringe, and the flask was submergedin a bath of acetone cooled to -78 C with dry ice. A 2.0 M solutionof DIPEA in THF (224 mL, 0.448 mol; Sigma-Aldrich) was addedwith stirring over 5 min, and the resulting mixture was stirred for anadditional 10 min. The dry ice-acetone bath was removed and replacedwith an ice-water bath. The mixture was stirred for an additional30 min then the ice-water bath was removed and the flaskwas resubmerged in the dry ice-acetone bath. The mixture wasstirred for 10 min at -78 C, then aldehyde 2 (50.4 mL, 71.7 g, 0.448mol; Oakwood Products) was added from a syringe. The resultingmixture was stirred for an additional 10 min before the dry ice-acetone bath was removed. The flask was then warmed to r.t., andthe mixture was stirred at r.t. for 3 h. The reaction was thenquenched by addition of sat. aq NH4Cl (50 mL), and the resultingbiphasic mixture was diluted with H2O (300 mL) and Et2O (200mL). The two phases were separated, and the aqueous fraction wasextracted with Et2O (2 × 300 mL). The organic fractions were combined,dried (Na2SO4), and concentrated by rotary evaporation togive alcohol 3 as a viscous oil.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Woydziak, Zachary R.; Fu, Liqiang; Peterson, Blake R.; Synthesis; vol. 46; 2; (2014); p. 158 – 164;,
Bromide – Wikipedia,
bromide – Wiktionary

348-57-2, name is 1-Bromo-2,4-difluorobenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 348-57-2

To a suspension of [1-] bromo-2,4-difluorobenzene (53.0 mmol, 6.00 mL) in concentrated [H2SO4] (38.5 mL) at [0 C] was added dropwise concentrated HN03 (34.0 mL) maintaining internal temperature below [20 C.] The resulting mixture was stirred for 10 min at [0 C,] then poured into ice/water with vigorous stirring. The mixture was extracted with [ET20] (3 x 100 mL). The combined organic extracts were washed with aqueous [NAHC03] solution (3 x 100 mL) and brine, dried over [MGSO4,] filtered and concentrated in vacuo. The crude product was purified by flash chromatography (EtOAc: hexanes 1: 9) to afford 5-bromo-2,4- difluoronitrobenzene as a yellow oil (12.2 g, [97percent). LH] NMR (400 MHz, [CDC13)] [5] 8.45 (t, 1H, J = 7.5 Hz), 7.16 (dd, 1H, J = 11.0, 8.6 Hz); ESMS [M/E] : 240,238, 223,221, 112

The synthetic route of 348-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNAPTIC PHARMACEUTICAL CORPORATIONs; WO2004/5257; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

In a 1 L round bottom flask equipped with a reflux condenser under argon, a mixture of 1,4-dibromo-2,5-difluorobenzene (53.7 g, 197 mmol), (2-methoxyphenyl)boronic acid (20 g, 132 mmol), potassium phosphate monohydrate (60.5 g, 263 mmol) in dimethoxyethane (DME) (590 mL) and water (65 ml) was bubbled with argon for 10 min, then tetrakis (1.521 g, 1.316 mmol) was added and the reaction mixture was refluxed at 82 C. for 8 hours. The reaction was monitored by liquid chromatography-mass spectroscopy (LCMS). The reaction mixture was cooled to room temperature and treated with water (200 ml). The aqueous layer was separated and extracted several times with ethyl acetate (300 ml each). The organic layer was washed with brine (200 mL), dried with Na2SO4, filtered, concentrated, and dried in vacuo. The crude product was chromatographed on a 220 g gold SiO2 column eluting with 0-40% EtOAc/Hexane to yield 5-bromo-2,4difluoro-2?-methoxy-1,1?byphenyl as clear oil (19.68 g, 50% yield).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; JI, Zhiqiang; TSAI, Jui-Yi; DYATKIN, Alexey Borisovich; LIN, Chun; US2019/233451; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCl2.2H2O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and NaOH 1N (100ml). After extraction with CH2CI2, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2/MeOH (95/5). The title compoundwas obtained as a cream powder (2.5g, 54.74%); m.p. 126-128C

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.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/111046; (2004); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

69321-60-4, name is 2,6-Dibromotoluene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 2,6-Dibromotoluene

24.1) 1-Benzylsulfanyl-3-bromo-2-methyl-benzene (Intermediate 83): 2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 1000C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography. Yield: 17g, 72 %

The synthetic route of 69321-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; WO2009/103440; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 67344-77-8, A common heterocyclic compound, 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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.

To a solution of 1-(3-bromophenyl)-N-methylmethanamine (6; 45.6 g, 228 mmol) in CH2Cl2 (700 mL) were added N-(tert-butoxycarbonyl)glycine (43.9 g, 251 mmol), WSCD*HCl (52.4 g, 274 mmol), and HOBt (37.1 g, 275 mmol). After being stirred at room temperature for 1 week, the mixture was diluted with water and the mixture was extracted with CHCl3. The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/EtOAc = 7:1 to1:1) to give the product (49.1 g, 60percent) as an oil. 1H NMR (CDCl3): this compound exists as a pair of rotamers at room temperature. d 1.44 (minor rotamer, 9H, s), 1.46 (major rotamer, 9H, s), 2.90 (major rotamer, 3H, s), 2.98 (minor rotamer, 3H, s), 3.96?4.06 (2H, m), 4.44 (minor rotamer, 2H, s), 4.57 (major rotamer, 2H, s),5.54 (1H, br s), 7.06?7.25 (2H, m), 7.28?7.49 (2H, m); MS (ESI) m/z [M+H]+ 357, 359.

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.

Reference:
Article; Yamaki, Susumu; Suzuki, Daisuke; Fujiyasu, Jiro; Neya, Masahiro; Nagashima, Akira; Kondo, Mitsuhiro; Akabane, Takafumi; Kadono, Keitaro; Moritomo, Ayako; Yoshihara, Kosei; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 187 – 201;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1295502-53-2,Some common heterocyclic compound, 1295502-53-2, name is 4,7-Dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole, molecular formula is C6Br2F2N2S, 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.

To a 25 mL dry two-necked flask was added 4,7-dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole (327 mg, 1 mmol). Tributyl(4-hexyl-2-thienyl)stannane (1.130 g, 2.5 mmol), and dissolved in dry and deoxygenated tetrahydrofuran (15 mL), The system replaces the air three times with nitrogen. Then tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (50 mg, 0.04 mmol) was added to the system. Replace the air three times with nitrogen again, Heating to 110 C reflux for 72 hours; After cooling, the substance is loaded onto the silica gel. Purification using hexane/chloroform (4:1) as mobile phase silica gel column chromatography. Obtained 0.232 g of a yellow solid;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole, its application will become more common.

Reference:
Patent; Nanchang Hangkong University; Qin Yuancheng; He Anwang; Du Wanjun; Zhou Dan; (21 pag.)CN109836437; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 59907-13-0, 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 59907-13-0 as follows.

Intermediate 5; 2-Fluoro-6-methylDhenylboronic acid; A 500 mL 3-neck round bottom flask, equipped with a magnetic stirring bar, thermometer, and nitrogen gas inlet, was charged with 2-bromo-1-fluoro-3-methylbenzene (6.95 g, 36.80 mmol), B(O1Pr)3 (10.38 g, 12.7 mmol), and 60 mL of anhydrous ether under nitrogen. The mixture was cooled to -70 0C with a dry ice/acetone bath, then a solution of 1BuLi (1.7 M in pentane, 47.6 mL, 80.96 mmol) was added dropwise keeping internal temperature below -50 0C. The mixture was warmed to -5 0C and stirred for 30 min., then 35 mL of 5M HCI was added and stirred at room temperature for an additional 30 min. The mixture was extracted with MTBE (3×70 mL), the extract was washed with brine (2×50 mL), and evaporated under reduced pressure keeping the temperature below 20 0C. The resulting residue was dissolved in a mixture of 100 mL of aqueous 2M NaOH and 50 mL of ether. The mixture was washed with ether (3×50 mL), and the aqueous layer was carefully acidified with cone. HCI to pH 1 in an ice bath. The resulting precipitate was collected by vacuum filtration, washed with cold water (2×10 mL), and dried under vacuum at room temperature to give 2- fluoro-6-methylphenylboronic acid (1.63 g) as a tan solid. M. P 110-112 0C; 1H NMR (300 MHz, DMSO-d6): delta 8.40 (2H), 7.21 (1H), 6.96 (1H), 6.87 (1H), 2.30 (3H).

According to the analysis of related databases, 59907-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2006/51410; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1193389-40-0, The chemical industry reduces the impact on the environment during synthesis 1193389-40-0, name is 1-(4-Bromophenyl)cyclobutanamine hydrochloride, I believe this compound will play a more active role in future production and life.

The free base of commercially available [1 -(4-bromo-phenyl)-cyclobutyl]-amine hydrochloride [CAS 1 193389-40-0] (8.99 g, 34.24 mmol) was prepared as follows: (8.99 g, 34.24 mmol) of the hydrochloride salt was taken up in DCM and washed sequentially with aqueous sodium bicarbonate and water and the organic portion was tried and concentrated.The crude amine was taken up in dry THF (120 mL) and diisopropylethylamine (17.62 mL, 102.71 mmol) under nitrogen and a solution of di-tert-butyldicarbonate (8.22 g, 37.66 mmol) in THF (20 mL) was added. The reaction was stirred at rt overnight. The mixture was partitioned between EtOAc and water and the extracted organic phase was washed with brine and concentrated in vacuo to give the title compound.

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-(4-Bromophenyl)cyclobutanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; INCE, Stuart; HAEGEBARTH, Andrea; POLITZ, Oliver; NEUHAUS, Roland; BOeMER, Ulf; SCOTT, William; WO2012/7345; (2012); A2;,
Bromide – Wikipedia,
bromide – Wiktionary