Category: 58534-95-5

Synthetic Route of 58534-95-5,Some common heterocyclic compound, 58534-95-5, name is 3-Bromo-2-fluoroaniline, molecular formula is C6H5BrFN, 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.

General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2-fluoroaniline, its application will become more common.

Reference:
Article; Lv, Fengping; Li, Zhi-Fang; Hu, Wenhao; Wu, Xiaohua; Bioorganic and Medicinal Chemistry; vol. 23; 24; (2015); p. 7661 – 7670;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 58534-95-5, A common heterocyclic compound, 58534-95-5, name is 3-Bromo-2-fluoroaniline, molecular formula is C6H5BrFN, 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.

[0467] To a mixture of 3-bromo-2-fluoroaniline (1.0 g), (5-acetyl-2-chlorophenyl)boronic acid (3.132 g), Pd(dppf)C12 (0.860 g), and K2C03 (3.64 g) under an atmosphere of argon was added dioxane (40 mL) and water (10 mL). The mixture was bubbled with argon for 5 mm and heated with stirring at 100 C overnight. The reaction mixture was then filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The remaining residue was purified by column chromatography (0-0.5% MeOH in DCM) to afford S3 (0.9 g) as orange-yellow oil.

The synthetic route of 58534-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (394 pag.)WO2017/35360; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 58534-95-5, name is 3-Bromo-2-fluoroaniline, 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 58534-95-5, category: bromides-buliding-blocks

To a solution of 3-bromo-2-fluoro-phenylamine (1.10 g, 5.67 mmol) in DCM (50 mL) was added pyridine (0.68 mL, 8.51 mmol), 3-chloro-4-methoxy-benzenesulfonyl chloride (1.37 g, 5.70 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHC03, saturated aqueous NH4CI, brine and dried over Na2S04. The organic solvent was removed under reduce pressure and the crude triturated with Et2O to give the title compound (1.63 g) as a white solid. HPLC (254 nm): Rt: 5.74 min. HRMS (ESI) calcd for C13H10BrCIFNO3S [M+Na]+ 415.9129, found 415.9135. 1H NMR (600 MHz, DMSO-d6) delta ppm: 3.93 (s, 3 H) 7.10 (td, J=8.10, 1.19 Hz, 1 H) 7.22 – 7.25 (m, 1 H) 7.31 (d, J=8.79 Hz, 1 H) 7.47 – 7.52 (m, 1 H) 7.66 (dd, J=8.70, 2.29 Hz, 1 H) 7.74 (d, J=2.38 Hz, 1 H) 10.37 (s, 1 H).

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Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BINDI, Simona; CARENZI, Davide; MOTTO, Ilaria; PULICI, Maurizio; (83 pag.)WO2017/220477; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary