Category: bromides-buliding-blocks

Synthetic Route of 3972-64-3, A common heterocyclic compound, 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, molecular formula is C10H13Br, 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 1. 6 M solution of nbutyllithium (0.85 mL, 1.36 mmol) was added to a solution of dicyclohexylamine (0.27 mL, 1.36 mmol) in toluene (5 mL). After stirring for 5 min, a mixture of cisltrans isomers of 2-methyl-cyclohexanecarboxylic acid 2- trimethylsilanyl-ethyl ester (269 mg, 1.11 mmol) was added. After stirring for 30 min, 1-bromo-3-tert-butyl-benzene (248 mg, 1.16 mmol) was added followed by the simultaneous addition of tri-tert-butylphosphonium tetrafluoroborate (31 mg, 107 /mol) and tris (dibenzylideneacetone) dipalladium (O)-chloroform adduct (51 mg, 49. 3, mol). The solution was placed into a preheated oil bath at 60 °C. After stirring for 20 h, the solution was diluted with 10percent aqueous hydrochloric acid, and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49: 1,24 : 1, and 23: 2 hexanes: ethyl acetate as the eluant to yield 375 mg (90percent yield) of a mixture of cisltrans isomers of 1- (3-tert-butyl-phenyl)- 2-methyl-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a yellow oil. Method [2] Retention time 3.67 min by HPLC and 3.75 min by MS (M+Na=397). Method [2] Retention time 3.77 min by HPLC and 3.85 min by MS (M+Na=397).

The synthetic route of 3972-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 167355-41-1, 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. 167355-41-1, name is 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

DI-TERT-BUTYLDICARBONATE (575. 7 mg, 2. 64 mmol) in methylene chloride (5. 0 mL) is added in one portion to a solution of methylene chloride (7. 0 mL) at room temperature that contains (RAC)-6-BROMO-1, 2, 3, 4-tetrahydronaphthalen-2-ylamine (591. 6 mg, 2. 62 mmol) and triethylamine (1. 1 mL, 7. 89 MMOL). After stirring at room temperature for 19 h in air, the resulting amber solution is diluted with methylene chloride (25 mL), washed with a saturated aqueous solution of sodium chloride (2 x 50 mL), dried over magnesium sulfate, and evaporated to dryness under reduced pressure to give the title compound as a pale yellow solid. The purity of isolated 29 was >95%, as determined by 1H NMR spectroscopy, and was used without further purification. mp 107-108 C. H NMR (CDCl3) : No.1. 45 (s, 9H, C (CH3) 3), 1. 70 (m, 1H, H-3), 2. 04 (m, 1H, H-3), 2. 55 (dd, J= 16. 5 Hz, 8. 5 Hz, 1H, H-1), 2. 84 (pseudo t, J= 6. 5 Hz, 2H, H-4), 3. 05 (dd, J= 16. 5 Hz, 5. 0 Hz, 1H, H-1), 3. 94 (br, 1H, H-2), 4. 58 (br, 1H, NH), 6. 91 (d, J= 8. 0 Hz, 1H, H-8), 7. 22 (m, 2H, overlapping H-5 and H- 7). 13C NMR (CDCl3) : No.27. 1 (CH2, C-4), 28. 4 (C (CH3) 3), 28. 7 (CH2, C-3), 35. 6 (CH2, C-1), 46. 0 (CH, C-2), 79. 4 (C (CH3) 3), 119. 6 (C-Br, C-6), 128. 9 (CH, C-7), 131. 0 (CH, C-8), 131. 5 (CH, C-5), 133. 3 (C-8a), 137. 8 (C-4a), 155. 3 (NHCO2). LCMS m/z calcd. for C15H2OBRN02 ([M] +) 325 ; found 311 ([M – C4H7 + CH3CN] +, 22%), 270 ( [M-C4H7] +, 81%), 267 ( [M- C5H702 + CH3CN] +, 43%), 226 ([M-C5H702] +, 100%), 209 ([M – C5H10NO2]+, 94%).

The synthetic route of 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WO2005/19228; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 3814-30-0, The chemical industry reduces the impact on the environment during synthesis 3814-30-0, name is (Bromomethyl)cyclopentane, I believe this compound will play a more active role in future production and life.

EXAMPLE 2 Preparation of 1-cyclopentylmethylimidazole Imidazole (6.8 g, 0.1 mol) was added to a solution of sodium (2.3 g, 0.1 mol) in dry ethanol (100 ml). This solution was stirred and heated to reflux when bromomethylcyclopentane (16.3 g, 0.1 mol) was added dropwise. Following the addition, the mixture was stirred and heated under reflux for 16 h. After cooling, the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in 2 M-hydrochloric acid (150 ml) and the solution washed with ether. The aqueous solution was basified with 10 M-sodium hydroxide solution, and the product extracted with chloroform (3*50 ml). The extracts were combined, dried (MgSO4), and the solution concentrated to afford a yellow oil. The oil was purified using a silica gel column and elution with ethyl acetate/methanol (9:1). The product fractions were combined and concentrated under reduced pressure to afford 1-cyclopentylmethylimidazole (1.9 g), which was further purified by distillation, b.p. 68-69/0.125 mmHg.

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Burroughs Wellcome Co.; US4317830; (1982); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 176317-02-5, 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. 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(4-1) Synthesis of 1-(3-methyl-3-hydroxy-1-butynyl)-2,3,4-trifluorobenzene Under nitrogen replacement, 247 g of 2,3,4-trifluorobromobenzene was dissolved in 740 ml of DMF, into which 247 mL of triethylamine, 3.7 g of tetrakistriphenylphosphine palladium (0), and 4.4 g of copper iodide (I) were added, and heated to 70C. To this, 108 g of 3-methyl-1-butyne-3-ol was added dropwise for 1 hour, and the mixutre was then stirred for 2 hours at room temperature, for 1 hour at 50C, for 30 minutes at 60C, and for 2 hours at 80C. Then, 500 mL of water was added and cooled to room temperature, to which 200 mL of concentrated hydrochloric acid was added. After this was extracted twice using ethyl acetate, the extract and the organic layer were mixed together, washed using water and a saturated saline solution in that order, and dried using anhydrous magnesium sulfate. After the solvent was evaporated under a reduced pressure, the residue was purified by distillation under a reduced pressure (78 to 84C / 0.65 to 0.70 mmHg) to obtain 229 g of 1-(3-methyl-3-hydroxy-1-butynyl)-2,3,4-trifluorobenzene as a yellow solid.

The synthetic route of 1-Bromo-2,3,4-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Ink and Chemicals, Incorporated; EP1640433; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4117-09-3, name is 7-Bromo-1-heptene, 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 4117-09-3, Safety of 7-Bromo-1-heptene

Typical procedure for the preparation of Grignard reagent: To a suspension of magnesium (0.13g, 5.32mmol) in anhydrous THF (1mL) was added dropwise 1-bromobutane (0.1g, 0.71mmol) at room temperature under an argon. After the reaction started, a THF solution of the remaining 1-bromobutane (0.57g, 4.19mmol/anhydrous THF 4mL) was dropwise into the reaction mixture at that temperature. After stirring for 50min, 0.8M of n-BuMgBr in THF was obtained. (The concentration was determined by the titration experiment.) (0038) Method A: To a suspension of CuCN (0.059g, 0.66mmol) in anhydrous THF (1mL) was added dropwise a THF solution of n-BuMgBr (0.8M, 0.83mL, 0.66mmol, prepared from n-BuBr and magnesium) at -78C under argon. After stirring for 5min, the mixture was warmed to -10C, and then stirred for 10min. The reaction mixture was again cooled to -40C, and to this mixture was added dropwise a solution of (E)-diethyl 2-fluoro-3-phenyl-2-propenylphosphate (0.086g, 0.3mmol) in anhydrous THF (2mL). After 15min, the reaction was quenched with an aqueous saturated NH4Cl solution and the whole was extracted with diethyl ether. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography to give 2-fluoro-3-phenyl-1-heptene (13a) (quant., 19F NMR yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromo-1-heptene, and friends who are interested can also refer to it.

Reference:
Article; Nihei, Takashi; Kubo, Yusuke; Ishihara, Takashi; Konno, Tsutomu; Journal of Fluorine Chemistry; vol. 167; (2014); p. 110 – 121;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 7073-94-1, A common heterocyclic compound, 7073-94-1, name is 1-Bromo-2-isopropylbenzene, molecular formula is C9H11Br, 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-Bromo-2-Isopropylbenzene (6.0 g, 30 mmol) was dissolved in dry toluene (70 mL), and ethyl cyanoacetate (6.8 g, 60 mmol) and sodium phosphate (15 g, 90 mmol) were added. The reaction mixture was degassed by bubbling with argon gas. Bis(dibenzylideneacetone) palladium(O) (0.35 g, 0.60 mmol) and tri-tert-butylphosphine (0.25 g, 1.2 mmol) were added. The reaction mixture was charged in a 500 mL sealed tube and heated to 90 C for 20 hours. The reaction was cooled to room temperature and filtered through a Celite pad. The filtrate was concentrated and the residue was dissolved in ethyl acetate (120 mL) followed by a washing with water (2 x 100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography provided the title molecule as a colorless liquid (4.4 g, 63%): XH NMR (400 MHz, CDCI3) delta 7.44 (d, J = 7.6 Hz, 1H), 7.38-7.36 (m, 2H), 7.24-7.22 (m, 1H), 4.97 (s, 1H), 4.30-4.21 (m, 2H), 3.14 (hep, J = 5.2 Hz, 1H), 1.30-1.23 (m, 9H); EIMS m/z 216 ([M-CH3]+).

The synthetic route of 7073-94-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; BAUM, Erich W.; FISCHER, Lindsey G.; GOLDSMITH, Miriam E.; CROUSE, Gary D.; RENGA, James M.; SPARKS, Thomas C.; (234 pag.)WO2016/99929; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3344-70-5,Some common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, molecular formula is C12H24Br2, 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 two-necked flask under argon, NaH (43.7 mmol) is put into suspension in anhydrous THF (100 ml). The reaction medium is cooled down in an ice bath and acetoethyl acetate is added dropwise (39.7 mmol). After stirring for 10 minutes at 0° C. n-BuLi is added dropwise (1.56 M; 43.7 mmol). Stirring is carried out for a further 10 minutes at ambient temperature before proceeding with alkylation.Dibromododecane (15.9 mmol) in solution in 20 ml of anhydrous THF is added dropwise to the previous solution. The reaction medium is allowed to return to ambient temperature and stirring is continued for 1 hour. Water is added followed by extraction with ether (3 times). The organic phase is washed with a saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The product is purified by chromatography on silica-gel eluting with AcOEt-Hexane (1-1). A white solid is obtained (Yield=65percent); M.p.=60° C.NMR 1H (200 MHz, CDCl3): d 4.16 (q, 4H, 2CH2), 3.41 (s, 4H, 2CH2), 2.50 (t, 4H, 2CH2), 1.56-121 (m, 30H).

The synthetic route of 3344-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CNRS; US6972343; (2005); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1003-99-2, These common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, 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.

The N-(t-butyloxycarbonyl)-4-piperidone (10.13 g, 50.8 mmol, 1.0 eq) and the 2-bromo-5-fluoroaniline (11.6Og, 61.0 mmol, 1.2 eq.) were weighed into a flask. Acetic acid (75 mL) was added, followed by trimethylsilyl cyanide (7.75 mL, 58.1 mmol, 1.14 eq.). The mixture was stirred at rt for 24 hr, and was then added to a mixture of 200 mL ice and 200 mL saturated ammonium hydroxide solution. The resulting mixture was extracted twice with methylene chloride, and the organic solution was dried over magnesium sulfate, filtered, and concentrated to provide 22.57g of crude product.

Statistics shows that 2-Bromo-5-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 1003-99-2.

Reference:
Patent; MERCK & CO., INC.; SUNESIS PHARMACEUTICALS, INC.; WO2006/44497; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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.

EXAMPLE 206 4-(3-Bromo-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile A mixture of 3.52 g (9.7 mmol) of 4-chloro-7-methoxy-6-nitro-3-quinolinecarbonitrile and 2.0 g (10.7 mmol) of 3-bromo-4-fluoro aniline in 150 ml of methoxyethanol was refluxed under nitrogen for 5.5 hours. The reaction mixture was diluted with ethyl acetate and wash with sodium bicarbonate solution and sodium chloride solution. The organic layer was dried with sodium sulfate and then solvent was removed under vacuum. The residue was chromatographed on silica gel eluding with mixture of ethyl acetate and methanol to give 3 g of yellow solid: mass spectrum (electrospray, m/e): 416.8 and 418.8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; American Cyanamid Company; US6384051; (2002); B1;,
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. 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