Tag: M.W=100-200

Reference of 51376-06-8,Some common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, molecular formula is C6H3BrN2O, 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.

[00779] Intermediate 85: 2,1 ,3-benzoxadiazol-5-amine[00780] In a dry, nitrogen purged 5-10 mL microwave tube were successivelly introduced 5-bromo-2,1 ,3-Benzoxadiazole (200mg, 1.01 mmol), Pd2(dba)3 (46mg, 0.OSmmol) and tri-tertbutylphosphonium tetrafluoroborate (58mg, 0.2Ommol) and toluene (1 mL). The tube was evacuated/backfilled with nitrogen and then sealed. Lithium bis(trimethylsilyl)amide (1.0 M in toluene, 2mL, 2mmol) was added and the reaction mixture was thermally heated at 50 C overnight. After cooling to room temperature, the reaction mixture was diluted with ether (2OmL) and thesilylamide was deprotected by adding 2-3 drops of 1 M HCI(aq). The mixture was transferred to a separatory funnel and washed with sat. aq. NaHCO3 (lOmL). The organic layer was dried over Na2504, filtered and concentrated in vacuo. The residue was purified via column chromatography using an eluent of 0-100% EtOAc in heptane. Three main fractions were collected containing the expected product and unprotected I partially deprotecetd silyl amide. The fractions were pooled,concentrated in vacuo and the residue dissolved in THF (1 mL). 1 M HCI(aq) (1 mL) was added and the mixture was stirred at room temperature for 1 hour. The mixture was made alkaline with 1 M NaOH(aq) and extracted with EtOAc (3 x 1 OmL). The combined organic layers were washed with brine (l0mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified via column chromatography using an eluent of 0-100% EtOAc in heptane to give 2,1 ,3-benzoxadiazol-5-amine (57mg, 0.42mmol, 42%) as a yellow-green solid.1H NMR (DMSO-d6, 400MHz) O/ppm: 7.76 (1H, dd, J= 9.5Hz, 0.6Hz), 7.14 (1H, dd, J= 9.5Hz,1.8Hz), 6.43 (2H, brs), 6.35 (1H, dd, J= 1.8Hz, 0.6Hz).MS Method 2: RT: 1.22 mi mlz 136.0 [M+H]

The synthetic route of 51376-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
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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. 39478-78-9, name is 5-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H8BrN

1-(6-Acetyl-pyridin-2-yl)ethanone [8.33 g (0.051 mol)], 20.0 g (0.107 mol) of 5-bromo-2-methyl-pheny.amine and 200 ml of dry toluene with a few crystals of para-toluenesulfonic acid were refluxed under the flow of the nitrogen using a Dean-Stark trap for 3 d until the calculated amount of the water was separated (1.84 mi). The solvent was removed in a rotary evaporator and the resultant reaction mixture was recrystallized from 50 ml of ethanol. The yield of 26 was 19.88 g (78%) as a pale yellow solid. 1H NMR (500 MHz, C6D6, TMS): delta 1.90 (s, 6 H, Me), 2.12 (s, 6 H, Me), 6.50 (m, 2H, Arom-H), 7.20 (m, 4H, Arom-H), 7.30 (t, 3JHH=7.8 HZ, 1 H1 Py-H), 8.40 (d, 3JHH=7.8 HZ, 2H, Py-H). 13C NMR (500 MHz, C6D6, (selected signals)): delta 167.4 (C=N). Anal. Calculated for C23H2IBr2N3 (MoI. Wi: 499.24): C, 55.33; H, 4.24; N, 8.42. Found: C, 55.48; H, 4.45; N, 8.53.

The synthetic route of 39478-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; WO2007/59015; (2007); A1;,
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Electric Literature of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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.

REFERENCE EXAMPLE 78 A stirred solution of 3-hydroxy-4-methoxy-benzaldehyde (5.74 g) in dry dimethylformamide (50 mL) is treated with cyclopentylmethyl bromide (7.34 g) and potassium carbonate (15 g), and the solution is heated at 60 C. for 24 hours. After cooling and filtration, the solution is evaporated to low bulk and dissolved in ethyl acetate (100 mL). The organic solution is washed with aqueous sodium hydroxide solution (4*50 mL; 2N) and water (2*50 mL), dried over magnesium sulfate, and evaporated to give 3-cyclopentyl-methoxy-4-methoxybenzaldehyde (6.5 g) in the form of a light brown oil. By proceeding in a similar manner, but using the appropriate quantity of isopropyl bromide, there is prepared 3-isopropoxy-4-methoxybenzaldehyde, in the form of a light golden oil. ?NMR (CDCl3): 9.85(s,1H), 7.46(dd,1H), 7.43(d,1H), 6.98(d,1H), 4.65(m1H), 3.94(s,3H),[1.41(d,6H)].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopentane, its application will become more common.

Reference:
Patent; Rhone-Poulenc Rorer Limited; US5935978; (1999); A;,
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Synthetic Route of 1073-06-9,Some common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, molecular formula is C6H4BrF, 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: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiI2 (3.1 mg, 0.01mmol, 5 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrerbar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA (60 muL, 2 equiv.)and N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) were subsequently added in this order. The solution was gently bubbled with ethylene balloon for approximately 30 seconds. The solution was then taken up into a 8 mL stainless steel syringe pre-purged with argon, and quickly assembled onto thestop-flow micro tubing, SFMT setup. Solution was pumped into the SFMT at 400 muL/min while maintaining approximately 1:1 gas-liquid slug flow at 250 PSI. Filled SFMT was then irradiated with blueLED (2 meter strip, 18 W) in a 100oC oil bath for 24 hours. The SFMT was wash with DCM (8 mL) and subjected to GC analysis (Figure S5). Then water (30 mL) was added to reaction mixture and extracted with DCM (10 mL) three times. Combined organic layer was successively wash with brine three timesand dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography to yield the product as a mixture of meso/dl isomers (which could not be separated by column chromatography).

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-3-fluorobenzene, its application will become more common.

Reference:
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
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Application of 1003-98-1, 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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

Pyridine (10.39 g, 131.35 mmol, 1.00 equiv) was added over a solution of 4- dimethylaminopyridine (1.618 g, 13.24 mmol, 0.10 equiv) in dichloromethane (80 mL). The reaction mixture was cooled down to 0 C and a solution of cinnamoyl chloride (21.85 g, 131.15 mmol, 1.00 equiv) in dichloromethane (66 mL) was added. The resulting solution was stirred for 15 min at 0 C and a solution of 2-bromo-4-fiuoroaniline (25.0 g, 131.57 mmol, 1.00 equiv) in dichloromethane (125 mL) was added dropwise. The cooling bath was removed and the mixture was allowed to react at room temperature for one additional hour. After quenching with 100 mL of H2O, the solids were collected by filtration to afford the desired product as yellow solid in 88% yield.

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

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
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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. SDS of cas: 1422-54-4

1-Bromo-3-fluoro-2-methylbenzene (388mg, 2.05mmol), and (4-methoxyphenyl)methanol 5 (0.51 1 mL, 4mmol) were dissolved in DMF (5ml_) in a microwave vessel. Sodium hydride as a 60% dispersion in mineral oil (164mg, 4.0mmol) was added portionwise under a flow of nitrogen over 10min. The reaction vessel was then sealed and heated at 18O0C for 900s. The crude reaction mixture was poured onto 1 :1 wate?brine (6ml_) and DCM (1 OmL). The biphasic mixture was stirred at ambient temperature for 1 h and then the 10 organic and aqueous layers were separated. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 5:95 ethyl acetate:heptane afforded 1-bromo-3- (4-methoxybenzyloxy)-2-methylbenzene (289mg, 0.9mmol, 46%).

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

Reference:
Patent; N.V. ORGANON; WO2007/63071; (2007); A1;,
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Application of 39478-78-9,Some common heterocyclic compound, 39478-78-9, name is 5-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Step 1 Preparation of 3-amiotano-4′-chloro-4-methylbiotaphenylTeirakiotas(triotapnenylphosphiotane)palladiotaum (0) (3 7 g, 0 003 mol) and 4-chlorophenylboroniotac acid (20 2 g, 0 13mol) are added to a solution of 5-bromo-2-methylaniotaliotane (20 g, 0 1 mol) in 1 ,2- dimethoxyethane (200 ml) After stirring the reaction mixture for 15 minutes at 2O0C, a solution of 20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is heated at reflux for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 3-amino-4′-chloro-4-methylbiphenyl (21.0 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2008/145336; (2008); A1;,
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Related Products of 4333-56-6, 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. 4333-56-6, name is Bromocyclopropane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of bromocyclopropane (Aldrich, 4.2 g, 35 mmol) in tetrahydrofuran (15 mL), magnesium turnings (Aldrich, 0.795 g, 33.1 mmol) were added in three equal portions at room temperature while the reaction was controlled with a water bath so that slight boiling of the solvent was maintained. _

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

Reference:
Patent; Chu, Xin-Jie; Ding, Qingjie; Jiang, Nan; Kim, Kyungjin; Lovey, Allen John; McComas, Warren William; Mullin JR., John Guilfoyle; Tilley, Jefferson Wright; US2004/6058; (2004); A1;,
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Synthetic Route of 21120-91-2, 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. 21120-91-2, name is 7-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

7-bromobicyclo[4.2.0]octa- 1 ,3,5-triene (10.0 g,54.6 mmol) and ethylene glycol (100 mE) were added to a250 mE round-bottom flask. The biphasic mixture wascooled to 0 C. followed by the slow addition of solid silver(I) tetrafluoroborate (11.7 g, 60.1 mmol) to maintain a temperature of about 30 C. After addition, the reaction mixture was stirred at 50 C. for 3 hrs. Once cooled down to room temperature, 200 ml water and 400 ml ether were added. The resulting mixture was filtered through celite. The organic layer was washed three times with each 300 ml water and then dried over Na2504 and concentrated to give an oil. The oil was purified by column chromatography on silica gel using 5% ethyl acetate in hexanes (4.66 g). The product had the following characteristics: ?H-NMR (400 MHz, CDC13): oe 7.36-7.27 (m, 1H), 7.27-7.20 (m, 2H), 7.15 (dp, J=7.2, 1.0 Hz, 1H), 5.20-5.03 (m, 1H), 3.90-3.61 (m, 4H), 3.56-3.39 (m, 1H), 3.21- (m, 1H), 2.23-1.98 (br s, 1H). ?3C-NMR (101 MHz, CDC13): oe 145.64, 142.42, 129.49, 127.10, 123.54, 122.70, 76.96, 69.75, 61.91, 38.53

The synthetic route of 7-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow Global Technologies LLC; Grigg, Robert David; Spencer, Liam P.; Kramer, John W.; Liu, Chun; Mukhopadhyay, Sukrit; Devore, David D.; Feng, Shaoguang; Feng, Jichang; Zhu, Minrong; (27 pag.)US2018/212180; (2018); A1;,
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Synthetic Route of 59907-12-9, A common heterocyclic compound, 59907-12-9, name is 1-Bromo-2-fluoro-3-methylbenzene, molecular formula is C7H6BrF, 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.

1-Bromo-3-bromomethyl-2-fluorobenzene Obtained according to Example E but starting from 1-bromo -2-fluoro- 3-methylbenzene (prepared according to M. S. Newman and R. Kannan, J. Org. Chem., 1976, 41, 3356) and distilling the final product at 20 mm Hg. Yd.: 66% B.p.20 =95-105 C. 1 H N.M.R. (CDCl3): 4.4 (2H, s), 6.6 to 7.6 (3H, m).

The synthetic route of 59907-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lipha, Lyonnaise Industrielle Pharmaceutique; US5489592; (1996); A;,
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