Category: 51776-71-7

Some common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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. category: bromides-buliding-blocks

Example 33A 1-Bromo-4-[bromo(difluoro)methyl]benzene With exclusion of oxygen, a solution of 14.0 g (67.63 mmol) of 1-bromo-4-(difluoromethyl)benzene [CAS 51776-71-7] and 25.3 g (142 mmol) of N-bromosuccinimide (NBS) in 190 ml of tetrachloromethane is irradiated with a sun lamp. During this, the solvent reaches its boiling point. It is irradiated under reflux for 24 hours. The mixture is then allowed to cool to room temperature and precipitated succinimide is filtered off. The filtrate is again mixed with 25 g of NBS and irradiated once more with exclusion of oxygen under reflux for 24 hours. Cooling is followed by filtration again, and the filtrate is concentrated to dryness. 18 g of an orange-colored oil are obtained as crude product, which is purified further by vacuum distillation at 13 mmHg. 12.7 g (44.4 mmol, 66% yield) of a colorless oil are obtained. Boiling point (13 mmHg): 90-92 C. 1H-NMR (300 MHz, DMSO-d6, o/ppm): 7.79 (2H, d), 7.63 (2H, d). MS (ESI): 205/207 (M-Br+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51776-71-7, its application will become more common.

Reference:
Patent; BAYER HEALTHCARE AG; US2009/227640; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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: Under an argon atmosphere, degassed CCl4 (0.35 M) was addedto a round bottom flask containing the corresponding difluoromethyl arene (1.0 equiv.) and N-Bromosuccinimide (1.7 equiv.). The reaction mixture was irradiated by the light of a 120 W sun lamp (approx. 12 cm distance between lamp and reaction flask) for 1-30 days before being quenched with Na2S2O3 (sat. aq.) and extracted with CH2Cl2 (330 mL). The combined organic layers were washed with brine, dried over MgSO4 and the solvent was removed under reduced pressure. Purification by column chromatography afforded the desired bromodifluoromethyl arenes. 1-Bromo-4-(bromodifluoromethyl)benzene (3c). Following the general procedure B from 4-bromobenzaldehyde with a reaction time of 2 days. Purification by column chromatography (SiO2; pentane/Et2O 100:1) afforded 1-Bromo-4-(difluoromethyl)benzene as a colorless oil (1.05 g, 81%). 1H NMR (400 MHz,CDCl3, TMS): d = 7.62-7.58 (m, 2H), 7.41-7.36 (m, 2H), 6.61 (t, J(H,F) = 56.3 Hz, 1H). 13C NMR (100 MHz, CDCl3, TMS): d = 133.4 (t, J(C,F) = 22.8 Hz), 132.1, 127.4 (t, J(C,F) = 6.0 Hz), 125.3 (t, J(C,F) = 2.5 Hz),114.3 (t, J(C,F) = 239.2 Hz). 19F NMR (377 MHz, CDCl3): d =111.10(d, J(F,H) = 56.3 Hz). (EI) m/z (rel intens) 207.89 (M+, 81Br, 100),205.98 (M+, 79Br, 93), 127.23 (M+-Br, 49). From 1-Bromo-4-(difluoromethyl)benzene with a reaction time of 9 days. Purification by column chromatography (SiO2; pentane) afforded the title compound as a colorless oil (745 mg, 82%). 1H NMR (400 MHz,CDCl3, TMS): d = 7.62-7.58 (m, 2H), 7.50-7.46 (m, 2H). 13C NMR(100 MHz, CDCl3, TMS): d = 137.3 (t, J(C,F) = 24.2 Hz), 132.1, 126.1 (t, J(C,F) = 5.1 Hz), 126.0 (t, J(C,F) = 1.7 Hz), 117.8 (t, J(C,F) = 303.7 Hz). 19FNMR (377 MHz, CDCl3): d =44.05 (s). (EI) m/z (rel intens) 207.19(M+79Br-Br, 96), 205.17 (M+81Br-Br, 100), 126.23 (M+-Br2, 47).

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; Bermejo Gome, Antonio; Gonzalez, Miguel A. Cortes; Luebcke, Marvin; Johansson, Magnus J.; Schou, Magnus; Szabo, Kalman J.; Journal of Fluorine Chemistry; vol. 194; (2017); p. 51 – 57;,
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. 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H5BrF2

B. Synthesis of 2-[4-(difluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(11) (25.25 g, 34.5 mmol) was added in one portion to a degassed mixture of 1-bromo-4-(difluoromethyl)benzene (160 g, 0.77 mol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (392.5 g, 1.55 mol) and potassium acetate (303 g, 3.09 mol) in 1,4-dioxane (2.42 L), and the reaction was heated to 100 C. for 18 hours. The mixture was then cooled to room temperature and filtered through Celite, washing with ethyl acetate (3 L). The filtrate was concentrated in vacuo to give a dark brown oil. The reaction was repeated an additional 3 times, on batches of 50 g, 160 g and 156 g of 1-bromo-4-(difluoromethyl)benzene (total starting material, 526 g, 2.54 mol), and the combined crude products were purified twice by chromatography on silica gel (Gradient: 0% to 3% ethyl acetate in heptane) to provide a yellow-white solid (803 g). This was recrystallized from methanol (1.6 L) at -20 C., and the filtrate was concentrated to one-half its original volume, cooled, and the resulting solid was collected by filtration. The combined solids (426 g) were recrystallized from heptane (500 mL) at -20 C., then melted and poured into methanol (200 mL) cooled in a methanol-ice bath. The mixture was broken up and filtered to yield C5 as a solid. Yield: 250.7 g, 0.987 mmol, 39%. 1H NMR (400 MHz, CDCl3) delta 1.37 (s, 12H), 6.65 (t, J=56.4 Hz, 1H), 7.52 (br d, J=8.1 Hz, 2H), 7.92 (br d, J=8.0 Hz, 2H).

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:
Patent; Pfizer Inc.; US2012/214791; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

Example 38; 4-(4-Difluoromethyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; A mixture of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) (102 mg, 0.36 mmol), 1-bromo-4-difluoromethyl benzene (110 mg, 0.53 mmol), Cs2CO3 (174 mg, 0.53 mmol) and CuI (1 mg) in DMF (5 mL) was heated for 2 hr at 160 C. in the microwave. The mixture was filtered and the filtrate was purified by reverse phase chromatograph to give a white solid (18 mg, 12% yield). 1H NMR (400 MHz, CDCl3) delta 9.92 (d, J=2.02 Hz, 1H) 8.52 (s, 1H) 7.72 (dd, J=10.36, 1.77 Hz, 1H) 7.64 (d, J=8.34 Hz, 1H) 7.28 (s, 1H) 7.09 (t, J=7.96 Hz, 1H) 7.05 (s, 1H) 6.97 (s, 1H) 6.77 (d, J=2.02 Hz, 1H) 3.78 (s, 3H) 2.98 (s, 2H) 1.51 (s, 6H); LCMS for C22H21F2N3O3 m/z 414.00 (M+H)+.

The synthetic route of 51776-71-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2008/280875; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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.

In a 10 mL vial charged with [l-[(4,4-difluorocyclohexyl)methyl]-6-(3,5-dimethylisoxazol-4-yl)pyrrolo[3,2-b]pyridin-3- yl]boronic acid (51, 0.05 g, 0.13 mmol) and acetonitrile (4 ml) was added l-bromo-4- (difluoromethyl)benzene (0.05 g, 0.24 mmol), 1M aqueous potassium carbonate (2 ml), and [1, 1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.01 g, 0.01 mmol). The reaction mixture was heated at 140 C in a microwave reactor for 30 min. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine. Then, the organic layer was dried over magnesium sulfate and the drying agent removed by filtration. The volatiles were removed from the filtrate under reduced pressure and the crude material was purified by silica gel flash chromatography eluting with 0-50% ethyl acetate in hexane to provide product as a tan solid (P-0608, 18 mg, 28.6%) MS (ESI) [M+H+]+ = 472.0.

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:
Patent; ZHANG, Jiazhong; BUELL, John; CHAN, Katrina; IBRAHIM, Prabha, N.; LIN, Jack; PHAM, Phuongly; SHI, Songyuan; SPEVAK, Wayne; WU, Guoxian; WU, Jeffrey; WO2014/145051; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, 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 51776-71-7, category: bromides-buliding-blocks

Example 38:; phit’i-Difluoroinethyl-phenoxyJ^^-dimethyl^.S-dihydro-benzofuran-beta-carboxylic acid (1 -methyl-1 H-pyrazol-3-yl)-amide; A mixture of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1 -methyl-1 /-/-pyrazol-3-yl)- amide (31a) (102 mg, 0.36 mmol), 1-bromo-4-difluoromethyl benzene (110 mg, 0.53 mmol), Cs2CO3 (174 mg, 0.53 mmol) and CuI (1 mg) in DMF (5 mL) was heated for 2 hr at 16O0C in the microwave. The mixture was filtered and the filtrate was purified by reverse phase chromatograph to give a white solid (18 mg, 12% yield). 1H NMR (400 MHz, CDCI3) delta 9.92 (d, J=2.02 Hz, 1 H) 8.52 (s, 1 H) 7.72 (dd, .7=10.36, 1.77 Hz, 1 H) 7.64 (d, J=8.34 Hz, 1 H) 7.28 (s, 1 H) 7.09 (t, J=7.96 Hz, 1 H) 7.05 (s, 1 H) 6.97 (s, 1 H) 6.77 (d, J=2.02 Hz, 1 H) 3.78 (s, 3 H) 2.98 (s, 2 H) 1.51 (s, 6 H); LCMS for C22H21F2N3O3 m/z 414.00 (MH-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, 1-Bromo-4-(difluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/122482; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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. Formula: C7H5BrF2

General procedure: Protocol A: The 0.020 M, THF solution obtainedfrom a 0.30 mmol scale preparation of R?CF2 reagent was combined with an electrophile (i.e., substrate) (0.30 mmol) dissolved in 3.0 mE THF at -80 C. The reaction mixture was then allowed to warm to room temperature and allowed to stand for 10 minutes. The solution was poured into saturated NH4C1 in H20 (50 mE) and the organics extracted into DCM (3×50 mE). The organic extract was dried with Mg504, filtered, concentrated onto 3 grams of silica gel, and purified by flash chromatography as specified.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51776-71-7, its application will become more common.

Reference:
Patent; REGENTS OF THE UNIVERSITY OF MICHIGAN; Szymczak, Nathaniel; Geri, Jacob; US2020/2362; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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 stirred mixture of l-bromo-4-(difluoromethyl)benzene (0.76 g, 3.7 mmol), bis(pinacolato)diboron (1.13 g, 4.4 mmol), l,l’-bis(diphenylphosphino)ferrocene- palladium dichloride (0.31 g, 0.37 mmol), and potassium acetate (1.09 g, 11.1 mmol) in dry 1,4-dioxane (10.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 90 C and monitored with LC-MS and TLC. After 21 h, the reactions were cooled to rt then filtered through Celite. The organic solvent was removed under reduced pressure, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield a yellow liquid as 2-(4-(difluoromethyl)phenyl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane. 1H NMR (400 MHz, DMSO-d6) delta ppm 7.80 (2 H, m, J=8.0 Hz), 7.57 (2 H, m, J=8.0 Hz), 7.05 (1 H, t), 1.36 (12 H, s).

The synthetic route of 51776-71-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); 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. 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 51776-71-7

Step 2: To a 250mL round-bottom flask was added 150mL toluene, compound 12b (19g, 0.09mol, l .Oq), Benzyl mercaptan (12.5g, O. lmol, l . leq), DIPEA (23.7g, 0.18mol, 2.0eq), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (3.7g, 0.005mol, 0.05eq) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (5.3g, 0.009mol, O. leq). The reaction was heated to reflux for 15h. The reaction mixture was concentrated in vacuum and purified by column chromatography on silica gel eluted to afford the title compound 12c (15g). Yield: 65%.

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:
Patent; LIANG, Congxin; (62 pag.)WO2018/5713; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, 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 51776-71-7, Quality Control of 1-Bromo-4-(difluoromethyl)benzene

(1) A solution of 1-bromo-4-(difluoromethyl)benzene (5.00 g, 24.1 mmol) in THF (75 mL) was cooled to -78 C. while stirring, and a solution of n-butylithium in n-hexane (1.57 M, 16.9 mL, 26.6 mmol) was added dropwise and the resultant mixture was stirred for 30 minutes. After adding DMF (4.09 mL, 53.1 mmol) and elevating the temperature to 0 C. over 1 hour, the resultant solution was stirred for 14 hours while gradually returning the temperature to room temperature. The reaction solution was neutralized by adding an ammonium chloride aqueous solution and extraction was performed with diethyl ether twice. Organic fractions were combined and washed with a saturated salt solution and dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure and the resultant residue was purified by column chromatography to obtain 4-(difluoromethyl)benzaldehyde (2.49 g, 66%). 1H-NMR (CDCl3) delta: 10.08 (1H, s), 7.99 (2H, d, J=8.3 Hz), 7.70 (2H, d, J=8.3 Hz), 6.72 (1H, t, J=55.9 Hz).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Teijin Pharma Limited; HOSODA, Shinnosuke; UNOKI, Gen; WATANABE, Hidekazu; SASAKI, Kosuke; SHIBATA, Jun; YOKOYAMA, Emi; HORIE, Kyohei; TAKAGI, Kenichiro; (202 pag.)US2019/31628; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary