Bromides-buliding-blocks

3972-65-4,Some common heterocyclic compound, 3972-65-4, name is 1-Bromo-4-(tert-butyl)benzene, molecular formula is C10H13Br, 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: In a 25mL round bottom flask containing 5mL of ethyleneglycol, aryl halide (1 equiv), trimethoxyphenylsilane (1.5equiv), NaOH (3 equiv) and Pd NPs (0.2mol%) were takenand stirred at 100C for required time. The reaction masswas cooled to room temperature after reaction completion(as monitored by TLC), followed by the recovery of Pd NPsby centrifugation at 6000rpm for 30min. The product wasthen extracted using dichloromethane (2 ¡Á 20mL) and subjectedto water wash (1 ¡Á 20mL) and brine wash (1 ¡Á 20mL)followed by drying of the organic layer over Na2SO4.Thedried organic layer was concentrated in vacuo, and the productwas purified by column chromatography using n-hexaneand ethyl acetate as eluents to aford the corresponding productsin good to excellent yields. All the coupled productswere known molecules and were confirmed by comparingthe melting point, 1H NMR and LC-MS data with authenticsamples (see Supporting Information for details).

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

Reference:
Article; Kandathil, Vishal; Dateer, Ramesh B.; Sasidhar; Patil, Shivaputra A.; Patil, Siddappa A.; Catalysis Letters; vol. 148; 6; (2018); p. 1562 – 1578;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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. 766-81-4.

In a 100 mL roundbottom flask, LiHMDS (1.0 M in THF, 3.0 mL, 3.0 mmol, 1.1 equiv) was dissolved in 22 mL anhyd hexanes and cooled to 0 C. 1-bromo-3- ethynylbenzene (415 muL, 3.3 mmol, 1.2 equiv) was added and the reaction removed from the cold bath and stirred for 15 min. The reaction was recooled to 0 C, and (R,E)-N-(3-((tert- butyldiphenylsilyl)oxy)propylidene)-2-methylpropane-2-sulfinamide (1.15 g, 2.77 mmol, 1.0 equiv) was transferred via cannula into the reaction in 5.5 mL anhyd hexanes. The reaction was allowed to warm to room temperature with stirring for 12 h. Equal volumes of saturated aqueous NH4Cl and Et2O (20 mL each) were added to the reaction mixture. The layers were separated and the aq layer extracted with Et2O (3 ¡Á 20 mL) then EtOAc (1 ¡Á 20 mL). The combined organic extracts were washed with brine (1 ¡Á 20 mL), dried (Na2SO4), filtered, and concentrated by rotary evaporation. 1H NMR analysis of the crude sample indicated the product was produced in >20:1 d.r. Purification by silica flash chromatography (2:1 hexanes/EtOAc) yielded the N-propargyl sulfinamide as a sticky brown foam (1.05 g, 63%). TLC: Rf 0.47 (40% EtOAc/hexanes). [alpha] D :-10.4 (c 0.55, CHCl3). IR (ATR): 2958, 2931, 2858, 1590, 1556, 1473, 1428, 1111, 1073, 762, 703. 1H-NMR (600 MHz,): delta 7.67 (ddd, J = 8.1, 2.7, 1.4 Hz, 4H), 7.52 (t, J = 1.7 Hz, 1H), 7.44 (ddd, J = 8.0, 2.0, 1.0 Hz, 1H), 7.43- 7.39 (m, 2H), 7.39- 7.33 (m, 4H), 7.32 (dt, J = 7.7, 1.3 Hz, 1H), 7.16 (t, J = 7.9 Hz, 1H), 4.59 (q, J = 6.9 Hz, 1H), 3.91 (ddd, J = 10.5, 6.6, 5.1 Hz, 1H), 3.86 (ddd, J = 10.5, 6.4, 5.1 Hz, 1H), 3.61 (d, J = 7.4 Hz, 1H), 2.11- 1.96 (m, 2H), 1.21 (s, 9H), 1.06 (s, 9H). 13C- NMR (151 MHz,): delta 135.5, 134.4, 133.3, 133.3, 131.5, 130.4, 129.7, 129.6, 127.7, 127.7, 124.6, 122.0, 90.2, 83.6, 60.3, 56.3, 45.6, 39.5, 26.8, 22.5, 19.2. HRMS m/z calcd for C31H38NO2NaSiSBr ([M+Na]+) 618.1474; found 618.1462.

The synthetic route of 3-Bromophenylacetylene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE BROAD INSTITUTE, INC.; UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.; MCKERROW, James; DANDAPANI, Sivaraman; EDWANKAR, Rahul; TAN, Derek, Shieh; FOLEY, Corinne, N.; MOURA-LETTS, Gustavo; VERANO, Alyssa; CHAKRABARTI, Debopam; ROBERTS, Bracken; (258 pag.)WO2017/124087; (2017); 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. 3814-30-0, name is (Bromomethyl)cyclopentane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3814-30-0

To a solution of 3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7H)-one (300 mg, 1.71 mmol) in anhydrous DMF (5 mL) was added K2CO3 (355 mg, 2.57 mmol) and (bromomethyl)cyclopentane (335 mg, 2.05 mmol). The reaction was stirred at 65C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC- MS to yield 7-(cyclopentylmethyl)-3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7/-/)-one 210 mg (47%). NMR (DMSO-ds, 400 MHz): delta 7.53 (s, 1 H), 7.51 (d, J = 6.0 Hz, 1 H), 6.90 (d, J = 6.0 Hz, 1 H), 3.69 (d, J = 7.6 Hz, 2H), 2.29-2.24 (m, 2H), 1.58-1.45 (m, 6H), 1.22-1.19 (m, 2H), 1.00- 0.89 (m, 4H). LC-MS: (m/z) 258.2 (MH+) tR (minutes, method 3) = 2.24 minutes

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1559-88-2, The chemical industry reduces the impact on the environment during synthesis 1559-88-2, name is 3-Bromo-1,2,4,5-tetrafluorobenzene, I believe this compound will play a more active role in future production and life.

The yield of 2,3,5,6-tetrafluorophenyl magnesium bromide measured in the same manner as Example 1 was 85.2 mol % based on 1-bromo-2,3,5,6-tetrafluorobenzene.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-1,2,4,5-tetrafluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nippon Shokubai Co., Ltd.; US6235222; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

627871-16-3, Adding a certain compound to certain chemical reactions, such as: 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, 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 627871-16-3.

Step P5.1 : 1-Bromo-2-fluoro-4-methyl-5-(2,2,2-trichloro-ethyl)-benzeneTo a solution of vinylidene chloride (127 ml), tert-butyl nitrite (19 ml) and copper(ll)chloride (18.4 g) in acetonitrile (150 ml) was added a solution of 5-bromo-4-fluoro-2-methyl- phenylamine (Bioorganic & Medicinal Chemistry Letters (2006), 16(2), 457-460) (21.5 g) in acetonitrile (100 ml) dropwise below 200C. The reaction mixture was stirred at room temperature for 48 hours, poured on diluted HCI and extracted with tert-butyl methyl ether(3x). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1 :4). Yield: 29.20 g of 1-bromo-2-fluoro-4-methyl-5-(2,2,2-trichloro- ethyl)-benzene as an oil.1H-NMR (CDCI3): delta 2.42 (s, 3H), 3.93 (s, 2H), 7.00 (d, 3J(H,F)=9.2Hz, 1 H), 7.69 (d,4J(H,F)=7.0Hz, 1 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, 5-Bromo-4-fluoro-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2009/49851; (2009); A1;,
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. 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. 1435-51-4

Preparation 37 1,3-Dibromo-5-methoxybenzene Sodium methoxide (8.80 ml of a 4.5M solution in methanol, 41.0 mmol) was added dropwise to a stirred solution of 3,5-dibromofluorobenzene (5.00 g, 19.0 mmol) in N,N-dimethylformamide (95 ml) at 0 C. under nitrogen. The reaction was allowed to warm to room temperature, stirred for 1 hour and then concentrated under reduced pressure. The residue was dissolved in ether and the resulting solution was washed with water (3*300 ml) and brine (300 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide the title compound (5.13 g) as a white solid. 1H-NMR (300 MHz, CDCl3): delta=3.79 (S, 3H), 7.00 (s, 2H), 7.26 (s, 1H).

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; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, 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 2270-59-9. 2270-59-9

EXAMPLE 5 2-Methyl-5-nitro-2-pentene 5-Bromo-2-methyl-2-pentene (120 g, 0.736 m) is added dropwise to a solution of sodium nitrate (60.9 g, 0.883 m) in dimethylsulfoxide (700 ml) at room temperature under nitrogen. The mixture is stirred for 1 hour and treated with water (500 ml) and petroleum ether (1 l). The organic layer is dried (Na2 SO4) and evaporated in vacuo to give a pale yellow liquid (80.7 g). This material is purified by column chromatography on silica gel (800 g, petroleum ether) to give 2-methyl-5-nitro-2-pentene as a colorless liquid (45.4 g, 48%). ir (neat) 1550 cm-1; nmr (CDCl3) delta: 1.70 and 1.73 (both 0,6H, (CH3)2 C=C<), 2.5~2.93(m, 2H, CH2 4.35 (t, J=8 Hz, 2H, --CH2 --CH2 --NO2), STR7 Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5-Bromo-2-methylpent-2-ene. Reference:
Patent; Ortho Pharmaceutical Corporation; US4177194; (1979); A;,
Bromide – Wikipedia,
bromide – Wiktionary

1422-54-4, 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. 1422-54-4, name is 2-Bromo-6-fluorotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 42 Preparation of (4-bromo-2-fluoro-3-methylphenyl)dimethyl(phenyl)silane To a 100 mL flask charged with THF (30 mL) was added diisopropylamine (1.285 g, 12.70 mmol). The reaction flask was cooled to -78 C. in a dry ice acetone bath and n-butyllithium (0.746 g, 11.64 mmol) was added. After 40 min of stirring at -78 C., 1-bromo-3-fluoro-2-methylbenzene (2 g, 10.58 mmol) in THF (10 mL) was added dropwise. Once an additional 40 min at -78 C. had passed, chlorodimethyl(phenyl)silane (5.42 g, 31.7 mmol) was added in one portion, the dry ice/acetone bath was removed and the reaction mixture was allowed to warm to room temperature. The reaction mixture was neutralized with a 5% HCl solution and diluted with water (200 mL). The aqueous solution was washed with EtOAc (200 mL*2). The combined organic layers were dried over Na2SO4. Following filtration, the organics were concentrated and the resulting residue was purified by flash chromatography with a gradient eluent system of hexanes and EtOAc to yield a clear oil as a mixture of products that contained (4-bromo-2-fluoro-3-methylphenyl)dimethyl(phenyl)silane which was used without further purification (850 mg): ESIMS m/z 324 ([M+H]+1).

The synthetic route of 1422-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; KISTER, Jeremy; PETKUS, Jeffrey; ROTH, Joshua; SATCHIVI, Norbert M.; SCHMITZER, Paul R.; SIDDALL, Thomas L.; YERKES, Carla N.; US2014/274703; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

67567-26-4, The chemical industry reduces the impact on the environment during synthesis 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, I believe this compound will play a more active role in future production and life.

Sodiumperborate tetrahydrate (18.5 g, 0.12 mol, 5.0 eq) was suspended in glacial acetic acid (125 mL) and heated to 65 C. 4-Bromo-2,6-difluoroanilline 2 (5.0 g, 24.0 mmol, 1.0 eq) dissolved in glacial acetic acid (50 mL) was added slowly through an funnel over 4 h. After the addition the reaction mixture was heated for 3 h additional hours before a second portion of NaBO3¡¤4H2O (6.0 g, 30.0 mmol) was added. Then the mixture was stirred for 14 h and a third portion of oxidating agent (9.0 g, 45.0 mmol) was added. 9 h after the third addition full consumption of the starting material was indicated by TLC. After cooling the mixture to room temperature, the formed solid was removed by filtration. The filtrate was poured into ice-cold water (300 mL). The precipitated solid was filtered off and dried to give the product as yellow solid (3.40 g, 60%). TLC [Silica, hexane/CHCl3 (5:1)]: Rf = 0.31. 1H NMR (300 MHz, CDCl3): delta = 7.36-7.28 (m, 2H). 13C NMR (75 MHz, CDCl3): delta = 154.7 (dd, J = 265.7, 2.8 Hz), 126.4 (t, J = 11.0 Hz), 117.2 (dd, J = 22.7, 3.9 Hz), [C-NO2 is not detected]. 19F NMR (282 MHz, CDCl3): delta = -117.0 (d, J = 7.1 Hz). LRMS (EI): m/z = 237 (calcd. 237 for C6H2 79BrF2NO2 [M]+).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2,6-difluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wagner, Sally; Scheunemann, Matthias; Dipper, Karolin; Egerland, Ute; Hoefgen, Norbert; Steinbach, Joerg; Brust, Peter; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 97 – 108;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5, These common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, 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.

Under nitrogen atmosphere, diisopropylamine (25.2 g) was dissolved in THF (130 mL) and cooled to -70 ¡ã C. or lower. To the solution, a 1.6 M butyl lithium / hexane solution (130 mL) was added dropwise at a rate such that the internal temperature did not reach -65 ¡ã C., and then the mixture was stirred at -70 ¡ã C. or less for 30 minutes. Subsequently, a solution prepared by dissolving 2,3-difluorobromobenzene (40 g) in THF (150 mL) was added dropwise to the stirring reaction solution at a rate such that the internal temperature did not exceed -65 ¡ã C., For 1 hour. Subsequently, a solution of DMF (22.7 g) dissolved in THF (220 mL) was added dropwise at a rate such that the internal temperature did not become -65 ¡ã C. or higher, followed by stirring at -70 ¡ã C. or lower for 1 hour, then slowly And the mixture was heated to room temperature. 10percent hydrochloric acid and toluene were added to the reaction solution, the organic layer was separated, and the organic layer was washed with saturated brine. Sodium sulfate was added to the organic layer after washing and dried, and then the solvent was distilled off under reduced pressure to obtain a crude product (44.9 g) of 4-bromo-2,3-difluorobenzaldehyde.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 38573-88-5.

Reference:
Patent; DIC CORPORATION; TOJO, KENTA; KUSUMOTO, TETSUO; TAKATSU, HARUYOSHI; (13 pag.)JP6019595; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary