Category: 142808-15-9

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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H3BrF4

Example 20 Synthesis of TRV 1 166[00146] TRV 1166 (4-(3-(isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l- yl)(phenyl)methanoneTRV 1166[00147] Scheme for TRV 1 166[00148] 4-bromo-2-fluorobenzotrifluoride (0.5181 g, 2.13 mmol), isopropyl amine (0.22 mL, 2.56 mmol), DIPEA (0.56 mL, 3.2 mmol) and NMP (3 mL) were added to a tube. The tube was sealed and heated overnight at 100 C. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HCI (2x), saturated NaHC03, H20 and brine before drying with Na2S0 . The material was filtered and concentrated under reduced pressure to give 0.1521 g of crude oil which was a 4:6 mixture of starting material to product, respectively. This material was dissolved in NMP (3 mL), treated with D PEA (0.07 mL, 0.38 mmol) and isopropyl amine (0.2 mL) and heated in a sealed tube at 115 C overnight. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give 0.1656 g of crude oil Purification of this material was not required. This aniline (0.1544 g, 0.55 mmol), benzoylpiperazine hydrochloride (0.1496 g, 0.66 mmol) and NaOiBu (0.1586 g, 1.65 mmol) were added to a tube. The tube was evacuated and flushed with argon for three cycles. Toluene (1.7 mL) and NMP (1.0 mL) were then added and the mixture was degassed with argon for 30 minutes. Pd2(dba)3 (0.0101 g, 0.01 1 mmol) and BetaGamma AlphaRho (0.0137 g, 0.022 mmol) were then added, the tube was sealed and heated overnight at 80 C. After cooling, the mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give a crude oil. Purification of this material via flash chromatography (20 % EtOAc / hexane) gave 0.125 g (58 % yield) of TRV 1166 (4-(3- (isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l-yl)(phenyl)methanone[00149] NMR (700 MHz, CDC13) delta = 7.46-7.41 (m, 5H), 7.30 (d, J = 8.4 Hz, 1 H), 6.21 (dd, J = 8.4, 2.1 Hz, 1H), 6.16 (s, 1H), 4.12-4.1 1 (m, 1H), 3.93 (br s, 2H), 3.68-3.66 (m, 1H), 3.59 (br s, 2H), 3.33 (br s, 2H), 3.18 (br s, 2H), 1.24 (d, J = 6.2 Hz, 6H).

According to the analysis of related databases, 142808-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; YADAV, Arun; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2012/119035; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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. Recommanded Product: 142808-15-9

To a reaction vessel under a nitrogen atmosphere, 4-bromo-2-fluoro-1-(trifluoromethyl)benzene (2.28 g) and diethyl ether (70 ml) were added, and cooling was carried out to-70C. Thereto, a n-butyllithium (1.57 M) n-hexane solution (7.10 ml) was added dropwise in a temperature range of -70C to -65C, and stirring was carried out for another 1 hour. Subsequently, a diethyl ether (10 ml) solution of compound (T-9) (2.68 g) was added dropwise in a temperature range of -70C to -65C, and stirring was carried out for 4 hours while returning to room temperature. The resultant reaction mixture was poured into ice water (100 ml), and mixing was carried out. Toluene (100 ml) was added to separate layers into an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was sequentially washed with a 1 N hydrochloric acid solution, a saturated aqueous solution of sodium hydrogencarbonate and water, and drying over anhydrous magnesium sulfate was carried out. The resultant solution was concentrated under reduced pressure, and a residue was purified by fractionation by means of column chromatography (silica gel; heptane), and further purified by recrystallization from a heptane/Solmix A-11 mixed solvent, and thus (E)-1-(1,2-difluoro-2-[3-fluoro-4-(trifluoromethyl)phenyl]vinyl)-2 -fluoro-4-(4-propylcyclohexyl)benzene (1-1-25) (2.24 g) was obtained. The yield based on compound (T-9) was 57%. Chemical shifts according to 1H-NMR analysis were as described below, and the compound obtained could be identified to be (E)-1-(1,2-difluoro-2-[3-fluoro-4-(trifluoromethyl)phenyl]vinyl)-2 -fluoro-4-(4-propylcyclohexyl)benzene. Chemical shifts delta (ppm; CDCl3); 7.72 – 7.57 (m, 3H), 7.46 (dd, J = 7.65 Hz, J = 7.65 Hz, 1H), 7.10 (d, J = 8.05 Hz, 1H), 7.04 (d, J = 11.7 Hz, 1H), 2.52 (tt, J = 9.15 Hz, J = 3.15 Hz, 1H), 1.96 – 1.85 (m, 4H), 1.50 – 1.38 (m, 2H), 1.38 – 1.26 (m, 3H), 1.26 – 1.19 (m, 2H), 1.12 – 1. 01 (m, 2H), 0.91 (t, J = 7.30 Hz, 3H). A phase transition temperature of compound (1-1-25) obtained was as described below. Phase transition temperature: C 104 N 125 I.

The synthetic route of 4-Bromo-2-fluorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JNC Corporation; JNC Petrochemical Corporation; EP2522649; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 142808-15-9, These common heterocyclic compound, 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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.

a) S.S’-Difluoro-^-ttrifluoromethylH-biphenylamineTo a stirred solution of 2-fluoro-4-iodoaniline (7.0 g, 29.5 mmol), bis(pinacolato)diboron (9.8 g, 38.6 mmol) and potassium acetate (8.7 g, 88.6 mmol) in dimethylformamide (150 ml_) was added [1 ,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (0.66 g, 0.9 mmol). After purging with nitrogen, the reaction was heated to 80 0C and stirred for 4 h. 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (7.2 g, 29.6 mmol), potassium carbonate (10.2 g, 73.8 mmol), water (20 ml_) and [1 ,1’- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (0.66 g, 0.9 mMol) were added and the reaction stirred at 100 0C for 18 h. After cooling to room temperature, the reaction was evaporated to dryness under vacuum. The residue was taken up in ethyl acetate, filtered to remove insolubles, washed with water, brine, dried (Na2SO4), filtered and concentrated under vacuum. Purification by flash chromatography on silica gel (20% ethyl acetate/hexanes), trituration with hexane, filtration and drying under vacuum gave the title compound (4.93 g, 61 %) as a white solid: MS (ES) m/e 274.0 (M + H)+.

Statistics shows that 4-Bromo-2-fluorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 142808-15-9.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113432; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 142808-15-9 name is 4-Bromo-2-fluorobenzotrifluoride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 142808-15-9

Preparatory Example27 (3-Fluoro-4- (trifluoromethyl) phenyl) (1-methylcyclopropyl) methanone (Scheme 7): To a solution of 4-bromo-2-fluoro-1- (trifluoromethyl) benzene (0.34 g, 1.4 mmol) in THF (5 mL) at -78under N2was added a solution of isopropylmagnesi

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-fluorobenzotrifluoride, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO. LTD.; SHEN, Dong-Ming; DWYER, Michael; SINZ, Christopher J.; WANG, Deping; STACHEL, Shawn; PAONE, Daniel;

The chemical industry reduces the impact on the environment during synthesis 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, I believe this compound will play a more active role in future production and life. 142808-15-9

At -78 C., 181.07 ml of a 2.5M (452.7 mmol) solution of n-butyllithium were added dropwise to a solution of 63.9 g (452.7 mmol) of 2,2,6,6-tetramethylpiperidine in 833 ml of dry THF. The mixture was stirred at this temperature for 30 min. 100.0 g (411.5 mmol) of 4-bromo-2-fluoro-1-(trifluoromethyl)benzene were then added dropwise at -78 C. The mixture was stirred at this temperature for 2 h. 33.1 g (452.7 mmol) of DMF were then added dropwise at -78 C. The reaction mixture was then stirred for 2 h. For work-up, 300 ml of water were added to the contents. The mixture was extracted three times with in each case 200 ml of dichloromethane. The combined organic phases were washed with 300 ml of 1M hydrochloric acid and then with 300 ml of a saturated aqueous sodium chloride solution. The organic phase was dried and the filtrate was freed of the solvent. 96.2 g of the desired product were obtained.

The chemical industry reduces the impact on the environment during synthesis 142808-15-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; AHRENS, Hartmut; TIEBES, Joerg; WALDRAFF, Christian; DIETRICH, Hansjoerg; SCHMUTZLER, Dirk; GATZWEILER, Elmar; ROSINGER, Christopher; (33 pag.)US2017/107183; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

142808-15-9, Name is 4-Bromo-2-fluorobenzotrifluoride, 142808-15-9, 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.

a) 6-[3-Fluoro-4-(trifluoromethyl)phenyl]-8-nitro-3,4-dihydro-2(1 H)-quinolinoneTo a stirred solution of 4-bromo-2-fluoro-1-(trifluoromethyl)benzene (1.0 g, 4.1 mmol), bis(pinacolato)diboron (1.1 g, 4.3 mmol) and potassium acetate (1.2 g, 122 mmol) in dimethylformamide (50 mL) was added [1 ,1′- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (81 mg, 0.11 mmol). After purging with nitrogen, the reaction was heated to 80 0C and EPO stirred for 2 h. 6-bromo-8-nitro-3,4-dihydro-2(1 H)-quinolinone (example 77a, 1.0 g, 3.7 mmol), cesium fluoride (1.3 g, 8.4 mmol), and tetrakis(triphenylphosphine)palladium (0) (130 mg, 0.11 mmol) were added and the reaction stirred at 100 0C for 18 h. After cooling to room temperature, the reaction was evaporated to dryness under vacuum. The residue was taken up in ethyl acetate, filtered to remove insolubles, washed with 1 M aq hydrochloric acid, brine, dried (MgSO4), filtered and concentrated under vacuum. Purification by flash chromatography on silica gel (3% ethyl acetate/dichloromethane) gave the title compound (0.77 g, 59%) as a yellow solid. MS (ES) m/e 355.0 (M + H)+.; +/- 6-f3-Fluoro-4-(trifluoromethvnphenyl1-3-hyclroxy-3.4-dihvdro-2(1 H)-quinolinone 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (0.091 mL, 0.375 mmol), bis(pinacolato)diboror) (0.10 g, 0.394 mmol), potassium acetate (0.11 g, 1.12 mmol), dichloro[1 ,1 ‘-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.020 g, 0.027 mmol) in DMF (2.0 mL) were heated to 800C under nitrogen for 2.5 hours. After the reaction was cooled, dichloro[1 ,1’- bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.020 g, 0.027 mmol) was added followed by addition of + 6-bromo-3-hydroxy-3,4-dihydro- 2(1 H)-quinolinone (example 85b, 0.095 g, 0.392 mmol) and 2M Na2CO3 in water (0.98 mL). The reaction was heated to 800C. After 12 hours the reaction mixture was cooled and diluted with ethyl acetate, then washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude reaction mixture was purified using reverse-phase preparative HPLC (10% CH3CN/H2O to 100% CH3CN/H2O with 0.1% TFA) to give the title compound as a solid. 1H NMR (400MHz, D6-DMSO) delta 10.34 (bs, 1 H), 7.79 (m, 2H), 7.69 (m, 2H), 7.59 (d, J = 8.6Hz, 1 H), 6.96 (d, J = 8.3 Hz, 1 H), 5.58 (bs, 1 H), 4.18 (m, 1 H), 3.13 (dd, 1 H), 2.93 (dd, 1 H).

Statistics shows that 4-Bromo-2-fluorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 142808-15-9.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113432; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary