Category: 445303-69-5

Application of 445303-69-5,Some common heterocyclic compound, 445303-69-5, name is 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, molecular formula is C7H4BrF3, 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.

Preparation 4:4-[3-(DIFLUOROMETHYL)-4-FLUOROPHENYL]PYRIDINETo a mixture of 4-bromo-2-(diotafluoromethyl)-l-fluorobenzene (0.5 g, 2.24 mmol), 1- pyriotadyl-4-boroniotac acid (0.33 g, 2.69 mmol) and sodium carbonate (0.64 g, 5.6 mmol) in toluene/ethanol (1 : 1, 20 ml) under nitrogen, was added palladium tetrakis (0.13 g , 5 mol%). The mixture was heated at reflux for 16 h, cooled to ambient temperature and diluted with water (50 ml) and ethyl acetate (100 ml). The organic layer was separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases was evaporated to dryness and dissolved in aqueous hydrochloric acid (10%, 50 ml). The solution was washed with diethyl ether (2×40 ml), basified with aqueous sodium hydroxide (2M) and extracted with ethyl acetate (2×50 ml). The combined organic phases was dried (MgSO4) and evaporated to dryness to give the crude product. Purification by flash column chromatography (ethyl acetate/isooctane 2: 1) gave the title compound (0.34 g). MS m/z (rel. intensity, 70 eV) 223 (M+, bp), 222 (12), 204 (7), 172 (12), 145 (8).

The synthetic route of 445303-69-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; A. CARLSSON RESEARCH AB; WO2007/65655; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 445303-69-5, 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 445303-69-5 as follows.

2-(3-Difluoromethyl-4-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane The title compound was obtained according to example 342 as a colorless oil (54% yield) using 4-bromo-2-difluoromethyl-1-fluoro-benzene and bis(pinacolato)diboron as the starting materials. MS: m/e=272 (M+).

According to the analysis of related databases, 445303-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alanine, Alexander; Buettelmann, Bernd; Heitz Neidhart, Marie-Paule; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene; US2002/151715; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 445303-69-5,Some common heterocyclic compound, 445303-69-5, name is 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, molecular formula is C7H4BrF3, 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.

Preparation 4:4-[3-(DIFLUOROMETHYL)-4-FLUOROPHENYL]PYRIDINETo a mixture of 4-bromo-2-(diotafluoromethyl)-l-fluorobenzene (0.5 g, 2.24 mmol), 1- pyriotadyl-4-boroniotac acid (0.33 g, 2.69 mmol) and sodium carbonate (0.64 g, 5.6 mmol) in toluene/ethanol (1 : 1, 20 ml) under nitrogen, was added palladium tetrakis (0.13 g , 5 mol%). The mixture was heated at reflux for 16 h, cooled to ambient temperature and diluted with water (50 ml) and ethyl acetate (100 ml). The organic layer was separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases was evaporated to dryness and dissolved in aqueous hydrochloric acid (10%, 50 ml). The solution was washed with diethyl ether (2×40 ml), basified with aqueous sodium hydroxide (2M) and extracted with ethyl acetate (2×50 ml). The combined organic phases was dried (MgSO4) and evaporated to dryness to give the crude product. Purification by flash column chromatography (ethyl acetate/isooctane 2: 1) gave the title compound (0.34 g). MS m/z (rel. intensity, 70 eV) 223 (M+, bp), 222 (12), 204 (7), 172 (12), 145 (8).

The synthetic route of 445303-69-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; A. CARLSSON RESEARCH AB; WO2007/65655; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 445303-69-5, 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 445303-69-5 as follows.

2-(3-Difluoromethyl-4-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane The title compound was obtained according to example 342 as a colorless oil (54% yield) using 4-bromo-2-difluoromethyl-1-fluoro-benzene and bis(pinacolato)diboron as the starting materials. MS: m/e=272 (M+).

According to the analysis of related databases, 445303-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alanine, Alexander; Buettelmann, Bernd; Heitz Neidhart, Marie-Paule; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene; US2002/151715; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 445303-69-5,Some common heterocyclic compound, 445303-69-5, name is 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, molecular formula is C7H4BrF3, 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 10 mL microwave vial was added 4-(4-fluorophenyl)-l-(l-methyl-lH-imidazol-4- ylsulfonyl)pyrrolidin-3 -amine hydrochloride (100 mg, 0.277 mmol) and premixed tris(dibenzylidene- acetone)dipalladium(0)/sodium tert-butoxide/ 2,2′-bis(diphenylphosphino)-l ,1 ‘-binaphthyl (100 mg, 0.05:0.15:2), aldrich 715530). The solids were suspended in 1 ,2-dimethoxyethane, and 4-bromo-2- (difluoromethyl)-l -fluorobenzene (74.8 mg, 0.333 mmol) was added. The reaction vessel was capped and the reaction mixture was heated in a microwave (Biotage Initiator, maximum 400 Watts) for 15 min at 130C. The mixture was filtered through celite, concentrated, dissolved in 2 ml 50% methanol/dimethylsulfoxide, and purified by HPLC to provide the title compound. MS (ESI) m/z 469 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, its application will become more common.

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; ABBVIE INC.; AMBERG, Wilhelm; POHLKI, Frauke; LANGE, Udo; WANG, Ying X.; ZHAO, Hongyu H.; LI, Huan-Qiu; BREWER, Jason T.; ZANZE, Irini; DIETRICH, Justin; VASUDEVAN, Anil; DJURIC, Stevan, W.; LAO, Yanbin; HUTCHINS, Charles W.; WO2014/140310; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary