Category: 51437-00-4

Adding a certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, belongs to bromides-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 51437-00-4, category: bromides-buliding-blocks

Under N2 atmosphere, an oven-dried 4 mL vial was charged with 2-fluoro-5- bromotoluene (56.7 mg, 38.3 mu, 0.300 mmol, 1.00 equiv), palladium complex 1 (11.4 mg, 15.0 muetaiotaomicron, 5.00 mol ), Ag(bipy)2C104 (16.0 mg, 30.0 muetaiotaomicron, 10.0 mol ), and NFBS (0.189 g, 0.600 mmol, 2.00 equiv). Acetonitrile (0.75 mL, c = 0.40 M) was added and the reaction mixture was stirred in a sealed vial at 23 C for 24 h. Subsequently, triethylamine (30.5 mg, 42.0 mu, 0.300 mmol, 1.00 equiv) was added and the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with hexanes/EtOAc (19: 1 to 4: 1 with 1% triethylamine), to afford 71.0 mg of the mixture of the title compounds as a yellow solid (63% yield). [00232] The products could not readily be separated by silica gel chromatography or preparative TLC, so they were characterized as a mixture. Compounds 2p-2p-IV were assigned through a combination of 1-D TOCSY and NOESY experiments (see page S92- S93). Data for 2p and 2p-II and 2p-III: [00233] R/= 0.57 (hexanes/EtOAc 7:3 (v/v)). NMR Spectroscopy: 1H NMR (600 MHz, CDC13, 23 C, delta): 8.07 (d, J = 8.2 Hz, 1.3H), 8.00 (d, J = 8.2 Hz, 4H), 7.96 (d, J = 8.2 Hz, 0.4H), 7.91 (d, J = 8.2 Hz, 0.6H), 7.72-7.68 (m, 2.9H), 7.66-7.62 (m, 0.3H), 7.59-7.54 (m, 5.7H), 7.53-7.49 (m, 0.7H), 7.46-7.42 (m, 1.5H), 7.31-7.27 (m, 0.2H), 7.25-7.22 (m, 0.2H), 7.01 (dd, J = 8.7, 8.7 Hz, 0.45H), 6.87 (dd, J = 9.6, 9.6 Hz, 0.2H), 6.81 (d, J = 9.6 Hz, 1H), 5.01 (s, 0.3H), 2.30 (s, 3H), 2.21 (s, 0.2H), 1.84 (s, 1.0H). 13C NMR (125 MHz, CDC13, 23 C, delta): Peaks are not listed because the mixture of four compounds, as well as splitting of aryl carbons by 19F, precluded assignment. See S91 for spectrum. Mass Spectrometry: HRMS (ESI-TOF) (m/z): calcd for Ci9H15BrNNa04S2 ([M + Na]+), 505.9504, found, 505.9502.

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Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; NGAI, Ming-Yu; BOURSALIAN, Gregory, Bagrad; MCNEILL, Eric, Andrew; RITTER, Tobias; WO2015/31725; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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. Formula: C7H6BrF

In an atmosphere of nitrogen gas, 74.1 ml of a 1.57 M solution of n-butyllithium in hexane was added to a solution of 16.3 ml of N,N-diisopropylamine in 400 ml tetrahydrofuran at 0C, and the mixture was stirred at the same temperature for 30 minutes. After cooling to -78C, a solution of 20.0 g of 5-bromo-2-fluorotoluene in 40 ml tetrahydrofuran was added dropwise. After stirring at the same temperature for 1 hour, 11.2 ml of 3-fluorobenzaldehyde was added dropwise and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was neutralized with 1 N hydrochloric acid and diluted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane = 1:20), to give 20.6 g of the title compound as a colorless oil.1H-NMR ( 400 MHz, CDCl3 ) d 2.23 ( 3H, s ), 2.34 ( 1H, d, J = 4.0 Hz ), 6.06 ( 1H, d, J = 4.0 Hz ), 6.98 ( 1H, dt, J = 2.4, 8.0 Hz ), 7.12 ( 1H, d, J = 8.0 Hz), 7.17 ( 1H, d, J = 8.0 Hz ), 7.25 ( 1H, d, J = 6.0 Hz ), 7.31 ( 1H, dt, J = 6.0, 8.0 Hz ), 7.50 ( 1H, dd, J = 2.4, 6.0 Hz )

The synthetic route of 51437-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, Adding a certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, belongs to bromides-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 51437-00-4.

To an oven dried three neck flask was added Mg turnings (355 mg, 14.6 mg-at.) catalytic amount of iodine, and 20 mL THF. To the resulting mixture was added dropwise 4-bromo-1-fluoro-2-methyl-benzene (1.0 g, 0.005 mol) with heating to 62 C. After completing the addition of the aryl bromide, the mixture was stirred for an additional 30 min at 62 C. The THF solution of the prepared aryl magnesium bromide was cooled to -70 C. and succinic anhydride (1.0 g, 0.01 mmol) added as a solution in 10 mL THF. The mixture was vigorously stirred with warming to rt over 3 h and then hydrolyzed by the addition of 30 mL of 1M HCl. The resulting mixture was extracted with ethyl acetate (2¡Á20 mL). The combined organic layers were extracted with 5% aqueous K2CO3 (3¡Á10 mL) and the combined aqueous layers acidified with 1M HCl to pH3. A milky colloidal suspension was extracted with ethyl acetate (3¡Á30 mL) and the combined organic layers washed with brine (2¡Á20 mL). The solvent was evaporated under reduced pressure and the crude product used directly in the next step without further purification.LC/MS: tR=6.0 min. MS (API-ES) m/z 211 (M+H+).

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, 4-Bromo-1-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PanThera Biopharma, LLC; US2010/286125; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, Adding some certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4.

Example 10A Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate starting with 10.6 g (74.0 mmol) of methyl piperidine-4-carboxylate and 4.67 g (24.7 mmol) of 5-bromo-2-fluorotoluene, the general procedure [E] gives 2.74 g (40% of theory) of product. HPLC (method 1): Rt=3.48 min Examples 11A to 17A from the table below can be prepared in accordance with the general procedure [E]. General Procedure [F]: Hydrolysis of the N-arylpiperidine-4-carboxylic Esters 1.0 equivalent of the N-arylpiperidine-4-carboxylic ester is dissolved in dioxane, and 2.0 equivalents of 1N aqueous sodium hydroxide solution are added. The mixture is stirred at 80 C. for 16 hours, and after the reaction has ended (the reaction is monitored by analytical HPLC) the mixture is concentrated. The residue is then taken up in water and adjusted to pH=5 using 1N hydrochloric acid. The resulting precipitate is filtered off, washed with a little water and cyclohexane and dried at room temperature under high vacuum. If the purity of the product is not high enough, the product is purified by preparative HPLC on an RP phase.

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 51437-00-4.

Reference:
Patent; Bayer HealthCare AG; US2007/281953; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4. 51437-00-4

In the case of Q10-Br, the desired 2-fluoro-5-phenyl-toluene (S1=F) was prepared from phenylboronic acid and 2-fluoro-5-bromo-toluene via a Suzuki reaction, analogously to procedure A2. See scheme A3.

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 4-Bromo-1-fluoro-2-methylbenzene.

Reference:
Patent; Duphar International Research B.V.; US6225312; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, A common compound: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, belongs to bromides-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.

1.6 M n-BuLi in hexane (7.94 mL, 12.70 mmol) was added to a solution of bis ( isopropyl ) amine (2.246 mL, 15.87 mmol) in THF(dry) (10 mL) at -78 C. The mixture was stirred at -7.8 C under Ar for 30 min. The solution of 4-bromo-l-fluoro-2- methylbenzene (1.338 mL, 10.58 mmol) in THF was added. The mixture was stirred at -78 C under Ar for 1 h. Propan-2-one (0.935 mL, 12.70 mmol) was added. The mixture was stirred at – 78C under Ar for 2 h. The mixture was poured into IN HC1 aq. and extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 3% – 12% EtOAc in hexane) to give the title (4065) compound (1.780 g, 7.20 mmol, 68.1%) as white solids. (4066) 1H NMR (300 MHz, DMSO-d6) 5:1.-46 (6H, d, J = 1.1 Hz), 2.21 (3H, d, J = 2.6 Hz), 5.39 (1H, s), 7.32-7.42 (1H, m) , 7.55 (1H, dd, J = 6.8, 2.6 Hz) .

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, 4-Bromo-1-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; SHIOKAWA, Zenyu; YUKAWA, Tomoya; IMADA, Takashi; NEGORO, Nobuyuki; ODA, Tsuneo; SASAKI, Satoshi; NARA, Yoshi; SUZUKI, Shinkichi; SATO, Ayumu; ISHII, Naoki; SHIBUYA, Akito; NAKAGAWA, Yasuo; COLE, Derek; GIBSON, Tony; IVETAC, Anthony; SWANN, Steve; TYHONAS, John; (472 pag.)WO2018/30550; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, Adding some certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4.

Example 7 4-Fluoro-3-methyl-benzaldehyde 2.85 g of 5-bromo-2-fluorotoluene, 0.21 g of bis(triphenyl-phosphine)palladium dichloride and 1.53 g of sodium formate were placed in a flask fitted with a reflux condenser and a gas inlet tube, 15 ml of DMF were added and the mixture was stirred and heated at 110 C. while passing in CO. After conversion was complete (GC monitoring), the reaction mixture was allowed to cool to 21 C. and the catalyst was separated off by filtration through silica gel. This gave a crude product which contained >98% of 4-fluoro-3-methyl-benzaldehyde (percentage is based on the areas in the GC).

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 51437-00-4.

Reference:
Patent; Bayer Aktiengesellschaft; US6462242; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary