Bromides-buliding-blocks

1559-88-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1559-88-2 as follows.

A solution of 1-bromo- 2,3,5,6-tetrafluorobenzene (4.58 g, 20 mmol) in 100 mL of anhydrous THF was cooled to -100 C (liquid nitrogen/ EtOH) under nitrogen. Then 1.4M solution of sec-BuLi in cyclohexane (15 mL, 21 mmol) was added dropwise at -100 C to -90 C. The mixture was stirred at -100 C to -90 C for 10 min, then a solution of R-(+)-propylene oxide (1.51 g, 1.8 mL, 26 mmol) in 15 mL of THF was added dropwise at -100 C to -90 C, then the mixture was cooled to -105 C and a 46.5% solution Of BF3 in diethyl ether (4.18 mL, 30 mmol) was added dropwise. The mixture was stirred at -100 C to -90 C for 2 h, then the reaction was quenched with 20 mL of sat. aq. NH4Cl at -90 C. The mixture was stirred and warmed to 0 C overnight. Then 20 mL of water was added and mixture was extracted with EtOAc (2×60 mL), the extract was dried over Na2SO4 and evaporated to give crude oil, which was purified by column (silicagel, EtOAc/hexane 1 :9, Rf = 0.57 in EtOAc/hexane 3:7) to give (2R)-1-(2,3,5,6-tetrafluorophenyl)propan-2- ol (2.57 g, 62 %) as a white solid. 1H NMR (300 MHz, CDCl3): delta 6.96 (m, 1H), 4.1 1 (m, 1H), 2.89 (m, 2H), 1.47 (d, J = 5.46 Hz, 1H), 1.29 (d, J = 6.21 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1559-88-2, and friends who are interested can also refer to it.

Reference:
Patent; CHEMBRIDGE CORPORATION; WO2009/117097; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

61921-39-9, A common compound: 61921-39-9, name is 4-Bromotetraphene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 54 Synthesis of 4-(diphenylamino)benz[a]anthracene 190 mul (1 mmol) of chlorodi-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.4 g (50 mmol) of 4-bromobenz[a]anthracene, 10.2 g (60 mmol) of diphenylamine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60 C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80 C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. Recrystallisation five times from dioxane (about 8 ml/g); sublimation (p=5*10-5 mbar, T=280 C.). Yield: 12.7 g (32 mmol), 64.1%, purity 99.9% (HPLC), Tg=74.7 C.

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, 4-Bromotetraphene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Stoessel, Philipp; Buesing, Arne; Heil, Holger; US2010/187505; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

699-03-6, A common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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 solution of 4-bromo-N-methylbenzylamine (199 mg,1.00 mmol), 3-pyridylboroxine (163 mg, 0.518 mmol), sodium carbonate (2 M, 4mL) and tetrakis(triphenylphosphine)-palladium(0) (30 mg, 0.026 mmol) in 1,4-dioxane (50 mL) was refluxed for 18 h. The solvent was eliminated under reduced pressure and the crude material was dissolved in a mixture of CH2Cl2 and CH3OH (1:1, 10 mL) and filtered through celite. After evaporation of the solvent, the crude material was purified by flash column chromatography (hexanes: ethyl acetate 6:4 and 1 % NEt3) to afford 1 as yellow oil (165 mg, 83 %); 1HNMR (CD2Cl2, 500 MHz): delta = 8.83 ppm (dd, J = 2.4 and 0.7 Hz, 1H), 8.54 (dd, J = 4.8 and 1.6 Hz, 1H), 7.89 (ddd, J = 7.9, 2.3 and 1.7 Hz, 1H), 7.58-7.56(m, 2H), 7.45-7.43 (m, 2H), 7.35 (ddd, J= 7.9, 4.8 Hz and 0.8 Hz, 1H), 3.78 (s, 2H), 2.43 (s, 3H), 1.64 (s, 1H); 13CNMR (125 MHz, CD2Cl2): delta = 148.9 ppm, 148.8 141.2, 137.0,136.9, 134.6, 129.4, 127.5, 124.1, 56.1, 36.3; IR (NaCl): nu = 3300 cm-1, 3028, 2933, 2844,2790, 2360, 1918, 1684, 1653, 1577, 1559, 1517, 1474, 1429, 1396, 1354, 1188,1129, 1103, 1024, 1001, 848, 796, 711; MS (CI, CH5+): m/z (%) = 199 (100) [M+H]+,168 (20), MS (EI, 70 eV): m/z (%):198 (100) [M]+, 168 (66), 156 (40); HR-MS (EI, 70 eV): m/z =198.11338 [M]+: calcd for C13H14N2:198.11570.

The synthetic route of 699-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keller, Marco; Wolfgardt, Annette; Mueller, Christoph; Wilcken, Rainer; Boeckler, Frank M.; Oliaro-Bosso, Simonetta; Ferrante, Terenzio; Balliano, Gianni; Bracher, Franz; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 13 – 22;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 22385-77-9

To a solution of 3 (1.5 g, 5.6 mmol) in anhydrous toluene (30 mL), 1-bromo-3,5-di-tert-butylbenzene (1.8 g, 6.7 mmol), was added t-BuONa, (1.2 g 13.4 mmol), and P(t-Bu)3 (1.38 mmol, 2.8 mL of a 10 wtpercent hexane solution) under argon. After stirring under reduced pressure, Pd(dba)2 (0.16 g, 0.28 mmol) was added to the solution. The reaction mixture was stirred at 110 ¡ãC for 16 h under argon. The precipitated solid was removed by filtration, and then the residue was washed with toluene (30 mL). After addition of methanol, precipitation occurred in the solution. The solid residue after filtration was washed with methanol (30 mL), and then was recrystallized from acetone to yield 6b (2.2 g, 86percent) as a pale-yellow powder. 6b: mp: 197 ¡ãC; 1H-NMR (400 MHz, CDCl3): delta = 1.40 (s, 18H, DBC-N-Ph-C(CH3)3), 7.40 (s, 2H, aromatic ring), 7.52 (dd, 2H, J = 14.8, 7.6 Hz, aromatic ring), 7.59 (dd, 3H, J = 8.8, 3.6 Hz, aromatic ring), 7.70 (dd, 2H, J = 15.2, 7.2 Hz, aromatic ring), 7.84 (d, 2H, J = 9.2 Hz, aromatic ring), 8.03 (d, 2H, J = 7.6 Hz, aromatic ring), 9.27 (d, 2H, J = 8.8 Hz, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 31.474, 35.16, 112.04, 117.43, 122.04, 122.26, 123.35, 125.40, 126.65, 129.07, 129.11, 130.10, 136.23, 138.02, 152.77; FT-IR (nu cm-1): 3100, 3000, 2850, 1600, 1400, 1350, 1300, 1250, 900, 675; HRMS calcd. for C34H33N ([M+Na]+): 478.2505, found: 478.2506.

Statistics shows that 22385-77-9 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-3,5-di-tert-butylbenzene.

Reference:
Article; Hassan, Fathy; Kawamoto, Masuki; Salikolimi, Krishnachary; Hashizume, Daisuke; Hirose, Takuji; Ito, Yoshihiro; Tetrahedron Letters; vol. 59; 2; (2018); p. 99 – 102;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 344-03-6, name is 1,4-Dibromotetrafluorobenzene, molecular formula is C6Br2F4, 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. 344-03-6.

Synthesis of 3,3′,3″,3″‘-(3,6-dibromobenzene-1,2,4,5-tetrayl)tetrapyridine (1) To a stirred solution of 3-bromopyridine (1.0 g, 6.3 mmol) in anhydrous THF (30 mL) is dropwise added n-butyllithium (1.6M in hexane, 5.9 mL, 9.5 mmol) under nitrogen at -78¡ã C. After 1 h stirring, 1,4-dibromo-2,3,5,6-tetrafluorobenzene (0.43 g, 1.4 mmol) is added in a portion. Then, the reaction temperature is allowed to room temperature and stirs overnight. The reaction solution is quenched with water (200 mL), and the resulted mixture is extracted with chloroform. The combined organic layers are washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The mixture is purified on silica gel column chromatography using 5:1 (v/v) hexane/chloroform as eluent to give a white solid.

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

Reference:
Patent; Kyulux, Inc.; Aguilera-Iparraguirre, Jorge; Gomez-Bombarelli, Rafael; Hirzel, Timothy D.; Cheng, Shuo-Hsien; Suzuki, Yoshitake; Yang, Yu Seok; (108 pag.)US2019/58130; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, A common compound: 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of l-bromo-2-fluoro-4-(trifluoromethyl)benzene (200 mg; 0.82 mmol)[CAS 40161-54-4] in tetrahydrofuran (15 mL) cooled to -70 C was added dropwise a solution of 1.6M n-butyllithium in n- hexane (0.7 mL; 1.1 mmol). After agitation at -70 C for 1 hour, the reaction mixture was treated dropwise with a solution of teri-butyl 4-[methoxy(methyl)carbamoyl]piperidine-l-carboxylate (247 mg; 0.91 mmol) [CAS 139290-70-3] in tetrahydrofuran (5 niL). The reaction mixture was stirred for 0.5 hours at -70 C and then for 2 hours at room temperature. The reaction mixture was deactivated with a saturated aqueous ammonium chloride solution (20 mL), then ethyl acetate (30 mL) was added. The organic layer was separated, dried over Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel; petroleum ethenethyl acetate; 30:1 ; v/v) to afford teri-butyl 4-[2- fluoro-4-(trifluoromethyl)benzoyl]piperidine-l-carboxylate (180mg) as a white solid. MS m/z (+ESI): 320.1 [M-iBu+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-2-fluoro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; LANE, Heidi; RICHALET, Florian; EL SHEMERLY, Mahmoud; (169 pag.)WO2018/2220; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

58971-11-2, name is 3-Bromophenethylamine, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 58971-11-2

A mixture of 3-bromobenzeneethanamine (9.70 g, 48,5 mmole) and 2,6-lutidine (5.8 ml, 50.0 mmole) in dry CH2Cl2 (150 ml) was cooled to 0 0C. Trifluoroacetic anhydride (5.6 ml, 40 mmole) was added dropwise; the reaction was then warmed to room temperature and allowed to stir for 24 hours. Water (120 ml) was added to the reaction, the phases were separated, and the aqueous layer was extracted with CH2Cl2 (2 x 100 ml). The combined organic phases were washed successively with IN HCl (100 ml) and saturated NaHCO3 (100 ml), and then dried over Na2SO4, filtered, and concentrated in vacuo to provide the tile compound (12.3 g, 86%). The crude compound was used in subsequent steps. 1H NMR (400 MHz, CDCl3) delta 7.40 (d, J=8.0 Hz, IH), 7.36 (s, IH), 7.21 (t, J=7.6 Hz, IH), 7.12 (t, J=7.6 Hz, IH), 6.31 (br s, IH), 3.59 (q, J-6.8 Hz, 2H)5 2.87 (t, JK7.2 Hz, 2H).

Statistics shows that 58971-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Bromophenethylamine.

Reference:
Patent; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2007/61458; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

111721-75-6,Some common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-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.

Examples 14 and 15 2-({4-[(2,3-Dihydro[l,4]dioxino[2,3-c]pyridin-7- ylmethyl)amino]-l-piperidinyl}methyl)-9-fluoro-l,2-dihydro-4H-pyrrolo[3,2,l- iy]quinolin-4-one hydrochloride, Enantiomers 1 and 2,(a) N-(2-Bromo-3 -fluorophenyl)-3 -phenyl-2-propenamide; To a solution of 2-bromo-3-fiuoroaniline (5.29g, 27.8mmol) in acetone (12ml) was added potassium carbonate (5.75g, 41.8mmol) followed by water (15ml) and the stirred mixture cooled to 00C. Cinnamoyl chloride (4.63g, 27.8mmol) was added portionwise over 15min then the mixture stirred for a further 2h. After this time the reaction mixture was poured onto ice/water and the resulting precipitate collected and dried to yield a white solid (8.Ig). LC-MS: m/z 320/322 (MH)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-3-fluoroaniline, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/3690; (2008); 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 20.6 g (0.1 mol) of 4-(3,5-difluorophenyl)phenol in 200 mL of N,N-dimethylformamide in a 500 mL of three-necked flask, 4.8 g (0.12 mol) of 60% sodium hydride was added portionwise under nitrogen with stirring at 30 C., and then 16.3 g (0.1 mol) of cyclopentyl methyl bromide was added dropwise. After the reaction was stuffed for 20 hours, it was poured into 500 mL of water, and was extracted with hot petroleum ether (200 mL¡Á2). The combined organic phases was washed with water to neutral, and the solvent was then distilled off under reduced pressure. 15 g of 4-a as white crystals was obtained by recrystallization from ethanol. GC purity: 98.9%.

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

Reference:
Patent; SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO., LTD.; Yuan, Guoliang; Liang, Zhian; Wang, Kui; Hua, Ruimao; Wen, Gang; Zhang, Miaofang; Meng, Jinsong; (28 pag.)US9303208; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 68322-84-9

Example 43A 4-trans(2-bromo-4-trifluoromethyl-phenoxy)-cyclohexylamine To a stirred solution of trans-4-aminocyclohexanol (115 mg, 1 mmol) in DMF (3 mL) at 0 C. was added 60% NaH in mineral oil (120 mg, 3 mmol). The reaction mixture was stirred at 0 C. for 1/2 hour and then 3-bromo-4-fluoro-1-trifluoromethyl benzene (0.17 ml, 1.2 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 338 (M+H)+.

Statistics shows that 68322-84-9 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary