Category: 1435-51-4

Synthetic Route of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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.

l,3-Dibromo-5-fluorobenzene (10.2 g, 40.7 mmol) was dissolved in 1,4- dioxane. Pyridine-4-ylboronic acid (5 g, 40.7 mmol), tetrakis(triphenylphosphine)- palladium(O) (462 mg, 0.41 mmol), and K2CO3 (11.22 g, 81 mmol) were added, and the mixture was heated at 900C for 4 h. The reaction was diluted with EtOAc, washed with aq. NaHCO3 and dried and removed. Purification via column chromatography afforded 4-(3-bromo-5-fluorophenyl)pyridine (6 g, 59%). 1H NMR (400 MHz, CDCl3): delta 8.73 (d, IH), 8.58 (d, IH), 7.77 (dd, IH), 7.45 (s, IH), 7.34-7.31 (m, IH), 7.22 (t, IH), 7.18- 7.15 (m, IH).

Statistics shows that 1,3-Dibromo-5-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1435-51-4.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1435-51-4, 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. 1435-51-4 name is 1,3-Dibromo-5-fluorobenzene, 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.

A mixture of Pd(OAc)2 (88 mg, 0.394 mmol) and BINAP (294 mg, 0.473 mmol) in dioxane (8 mL) was stirred in a sealed tube for ~5 min. To the mixture was then added l,3-dibromo-5-fluorobenzene (0.496 mL, 3.94 mmol) and (tetrahydro-2H-pyran- 4-yl)methanamine hydrochloride (299 mg, 1.969 mmol), stirring was continued for additional ~5 min and KOtBu (486 mg, 4.33 mmol) was added. The resulting mixture was heated at 93 C for ~18 hrs. The reaction mixture was cooled to room temperature, diluted with EtOAc (-50 mL) and MeOH (-10 mL), filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 40 g, EtOAc/heptane = 5/95 to 30/70] providing 3-bromo-5-fluoro-N-((tetrahydro-2H-pyran- 4-yl)methyl)aniline (220 mg) as a colorless liquid. LCMS (m z): 289.9 [M+H]+; Rt = 1.03 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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 1435-51-4, name: 1,3-Dibromo-5-fluorobenzene

Preparation of 3-cyano-5-difluoromethyl-phenol step 8-; A solution of 10a, sodium methoxide (1 equivalent) and DMF were stirred overnight under an N2 atmosphere at RT. The volatile solvents were removed in vacuo and the residue partitioned between Et2O and water. The organic phase was washed with 5% NaOH, water and brine, dried (MgSO4), filtered and evaporated to afford 10b.

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, 1,3-Dibromo-5-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2006/223874; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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 mixture of tris(dibenzylideneacetone)dipalladium (0.20 g, 0.22 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene (0.13, 0.22 mmol) and cesium carbonate (5.0 g, 15.41 mmol) under N2 gas was added acetamide (0.90, 14.73 mmol), l,3-dibromo-5- fluorobenzene (2.8 g, 10.83 mmol) and dioxane (22 mL). The reaction mixture was heated at 8O0C overnight and concentrated under reduced pressure. Purification by flash chromatography (silica, 50:50 ethyl acetate/hexane) gave N-(3-bromo-5-fluorophenyl)acetamide (3.51 g, quantitative). Retention time (min) = 1.945, method [4], MS(ESI) 232.0 (M+Eta).

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Product Details of 1435-51-4

A solution of 28 (15.6 g, 0.05 mol) in Et2O (30 mL) was added dropwise at -78 C to a stirred solution of LDA, freshly prepared from diisopropylamine (5.5 g, 0.55 mol) and nBuLi (10 M, 5 mL, 0.05 mol) in THF (80 mL). After ca 30 min stirring at ca -78 C chlorodimethylsilane (5.0 g, 0.053 mol) was added slowly. The mixture was stirred for 30 min at -78 C and then was allowed to warm warm to ca. -50 C. 1 M aqueous H2SO4 (30 mL) was added with stirring. The organic phase was separated. The water phase was washed with Et2O (2 × 30 mL). The combined organic phase was dried over anhydrous MgSO4. It was filtered and evaporated under reduced pressure and the residue was subjected to a fractional distillation under reduced pressure. The crude product was obtained as a colorless liquid, b.p. 95-103 C (1 Tr). It tends to solidify partly when stored for a longer time at room temperature. Subsequent crystallization of this material from cold methanol (50 mL, -30 C) afforded pure product as a white solid, m.p. 28-30 C. Yield 13.5 g (73%). 1H NMR (400 MHz, CDCl3): delta 7.59 (s, 1H, Ph), 4.80-4.63 (m, 2H, SiH), 0.44 (dd, J = 3.9, 1.9 Hz, 12H, SiMe2) ppm. 13C NMR (101 MHz, CDCl3): delta 170.85 (d, J = 244.5 Hz), 132.84 (d, J = 3.5 Hz), 132.18 (d, J = 14.4 Hz), 124.42 (d, J = 38.8 Hz), -3.23 (d, J = 4.4 Hz) ppm. 19F NMR (376 MHz, CDCl3): delta -77.55 (m) ppm. Anal. Calcd for C10H15Br2FSi2 (370.20): C, 32.44; H, 4.08. Found: C, 32.23; H, 3.93.

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; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1435-51-4, A common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

General procedure: Palladium reagents were synthesized following the scheme of Figure 14 for generalprocedure A. In a nitrogen-filled glovebox, an oven-dried scintillation vial (1 0 mL), whichwas equipped with a magnetic stir bar and fitted with a Teflon screwcap septum, vascharged with RuPhos (2.5 equiv), a dihaloaryl compound (1 equiv) and cydohexane (1.2mL). Solid [(1,5-COD)Pd(CH2Si:Me3)] (2.5 equiv) was added rapidly in one portion and theresulting solution vvas stirred for 16 hat Jt. After this time, pentane (3 mL) was added andthe resulting mixture vas placed into a -20 C freezer for 3 h. The vial was then takenoutside of the glove box, and the resulting precipitate was filtered, washed with pentane (3 X3 mL), and dried under reduced pressure to afford the oxidative addition complex (Figure14)

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; BUCHWALD, Stephen, L.; PENTELUTE, Bradley, L.; ZHANG, Chi; (170 pag.)WO2017/151910; (2017); 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1,3-Dibromo-5-fluorobenzene

Ice bath, the 2M Isopropylmagnesium chloride (10 mL, 20 mmol) was dissolved in 5 mL of tetrahydrofuran, A solution of 1,3-dibromo-5-fluorobenzene 40a (4.0 g, 15.70 mmol) In tetrahydrofuran,Stirred for 2 hours, and then heated to 20 C reaction for 30 minutes. Cool down to 0 C,N, N-Dimethylformamide (2.5 mL, 31.50 mmol) was added dropwise,The reaction was stirred for 1.5 hours,The reaction was stirred at room temperature for 12 hours.The reaction was quenched by the addition of 20 mL of saturated ammonium chloride solution, extracted with ethyl acetate (50 mL of X3) and the organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure and eluted with silica gel column chromatography eluent system B The resulting residue was purified to give the title product 3-bromo-5-fluorobenzaldehyde 40b (2.57 g, yellow liquid), yield: 81.0%.

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI HENGRUI PHARM CO LTD; JIANGSU HENGRUI MEDICINE CO LTD; Lyu, HEJUN; DONG, QING; FEI, HONGBO; JIANG, HONGJIAN; SONG, PENG; (114 pag.)CN103030646; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-51-4, A common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

Sodium hydride (9.9 g, 0.414 mol, 95% dry) was added in portions to a stirred solution of benzyl alcohol (41.0 g, 0.394 mol) in THF (1.0 L) at room temperature under a nitrogen atmosphere and stirred for 1 h. To this solution was added dropwise 1,3-dibromo-5-fluorobenzene (100.0 g, 0.394 mol). After stirring overnight, the mixture was partitioned with H2O (600 mL) and EtOAc (4*600 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluding with hexanes afforded the sub-title compound (101.3 g, 75%) as a yellow oil. 1H NMR (300 MHz, CDCl3) delta7.30-7.48 (m, 5H), 7.18 (s, 1H), 7.06 (s, 2H), 4.99 (s, 2H).

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Inghardt, Tord; Johansson, Anders; Svensson, Arne; US2004/19033; (2004); A1;,
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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Safety of 1,3-Dibromo-5-fluorobenzene

Example 6 a) 20.0 g (78.8 mmol) 1,3-dibromo-5-fluoro-benzene, 16.3 g (78.8 mmol) 6H-benzimidazolo[1,2-a]benzimidazole and 43.5 g (0.315 mmol) potassium carbonate in 200 ml DMF are stirred for 17 h at 170 C. The reaction mixture is filtered hot and the precipitate from the mother liquor is filtered after cooling. The product is washed with water and ethanol and decocted with diethyl ether and ethanol. Yield 21.2 g (61%).1H NMR (400 MHz, THF-d8): delta 8.21-8.26 (m, 4H), 7.98-7.8.00 (m, 1H), 7.68-7.73 (m, 2H), 7.31-7.49 (m, 4H).

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2012/241681; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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 mixture of Pd(OAc)2 (88 mg, 0.394 mmol) and BINAP (294 mg, 0.473 mmol) in dioxane (8 mL) was stirred in a sealed tube for ~5 min. To the mixture was then added 1 ,3- dibromo-5-fluorobenzene (0.496 mL, 3.94 mmol) and (tetrahydro-2H-pyran-4- yl)methanamine hydrochloride (299 mg, 1 .969 mmol), stirring was continued for additional ~5 min and KOtBu (486 mg, 4.33 mmol) was added. The resulting mixture was heated at 93 C for ~18 hrs. The reaction mixture was cooled to room temperature, diluted with EtOAc (~50 mL) and MeOH (~10 mL), filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 40 g, EtOAc/heptane = 5/95 to 30/70] providing 3-bromo-5-fluoro-N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (220 mg) as a colorless liquid. LCMS (m/z): 289.9 [M+H]+; Rt = 1 .03 min.

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary