Category: 17318-08-0

17318-08-0, name is 5-Bromo-1,3-dichloro-2-fluorobenzene, belongs to chlorides-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. Recommanded Product: 5-Bromo-1,3-dichloro-2-fluorobenzene

1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (Intermediate Compound 9) (0328) (0329) 9 (0330) [0164] To a cooled (10 C) solution of 1-bromo-3,5-dichloro-4-fluorobenzene (1.10 kg, 4.51 mol) in THF (9.70 L) was added /-PrMgCI LiCI (3.64 L, 4.74 mol, 1.3 molar) while maintaining the internal temperature at < 20 C. The reaction was stirred for 2 hours with an internal temperature of 18 C, before cooling to - 9 C. Methyl trifluoroacetate (499 ml_, 4.96 mol) was added while maintaining the internal temperature < 10 C. Reaction was warmed to 20 C and stirred for 3 hours before it was quenched with 4 molar HCI (1.50 L). The biphasic mixture was stirred 2 hours before it was diluted with heptane (4 L). The reaction was mixed for 10 min. and the layers allowed to separate. The aqueous layer was removed extracted 1X 2 L EtOAc and the combined organic fractions were washed 1 X 4L 22% aq. NaCI and dried over MgS04 (1.5 kg) for 15 hours. The organic solution was filtered and concentrated in vacuo. The residue was dissolved in toluene (4 L) and concentrated in vacuo. The resultant oil was dissolved in toluene (4 L) and concentrated in vacuo a second time to give 1.06 kg of 1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (89%) that was 91% pure. (0331) [0165] Note that the yields for smaller scale reactions have ranged between 60 - 94% for this experiment. (0332) [0166] 1H NMR (400MHz, CHLOROFORM-d) delta = 8.06 (dd, J=0.8, 6.1 Hz, 2H). (0333) [0167] Note that the hemiacetal hydrate can be detected in the 1H NMR as a doublet at delta = (0334) 7.69. The synthetic route of 17318-08-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AVISTA PHARMA SOLUTIONS, INC.; SPEAKE, Jason, D.; PANDI, Bharathi; OGBU, Cyprian, O.; ADAMS, Jeffrey, A.; MOORE, III, Joseph, A.; PERALAS, Joe, B.; LI, Keqiang; (50 pag.)WO2017/201134; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 17318-08-0, name is 5-Bromo-1,3-dichloro-2-fluorobenzene, molecular formula is C6H2BrCl2F, 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: chlorides-buliding-blocks

To an oven dried 8 mL vial with teflon cap purged with N2 was added Zinc dust (298 mg, 4.56 mmol), DMF(1.5 mL), and iodine (57.8 mg, 0.228 mmol). To this mixture was added (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (500 mg, 1.519 mmol), immediately followed by iodine (57.8 mg, 0.228 mmol).Pd2(dba)3 (69.6 mg, 0.076 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (62.4 mg, 0.152mmol), 5-bromo-1,3-dichloro-2-fluorobenzene (556 mg, 2.279 mmol) and the reaction mixture was allowedto stir at rt for 16 h. The crude mixture was diluted in 30 mL of EtOAc and DMF was removed using fouraqueous washes. The organic phase was dried over anhydrous sodium sulfate. The solution was filtered andconcentrated and the crude product was purified by silica gel chromatography using 100% hexanes to 30%EtOAc/Hexanes. The desired product was obtained as a pale yellow oil, (S)-methyl 2-((tertbutoxycarbonyl)amino)-3-(3,5-dichloro-4-fluorophenyl)propanoate, 0.102 g which was taken into next stepdirectly.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17318-08-0, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; Miller, Michael Matthew; Mapelli, Claudio; Allen, Martin Patrick; Bowsher, Michael S.; Boy, Kenneth M.; Gillis, Eric P.; Langley, David R.; Mull, Eric; Poirier, Maude A.; Sanghvi, Nishith; Sun, Li-Qiang; Tenney, Daniel J.; Yeung, Kap-Sun; Zhu, Juliang; Reid, Patrick C.; Scola, Paul Michael; (892 pag.)US9308236; (2016); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 17318-08-0, name is 5-Bromo-1,3-dichloro-2-fluorobenzene, molecular formula is C6H2BrCl2F, 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: chlorides-buliding-blocks

To an oven dried 8 mL vial with teflon cap purged with N2 was added Zinc dust (298 mg, 4.56 mmol), DMF(1.5 mL), and iodine (57.8 mg, 0.228 mmol). To this mixture was added (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (500 mg, 1.519 mmol), immediately followed by iodine (57.8 mg, 0.228 mmol).Pd2(dba)3 (69.6 mg, 0.076 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (62.4 mg, 0.152mmol), 5-bromo-1,3-dichloro-2-fluorobenzene (556 mg, 2.279 mmol) and the reaction mixture was allowedto stir at rt for 16 h. The crude mixture was diluted in 30 mL of EtOAc and DMF was removed using fouraqueous washes. The organic phase was dried over anhydrous sodium sulfate. The solution was filtered andconcentrated and the crude product was purified by silica gel chromatography using 100% hexanes to 30%EtOAc/Hexanes. The desired product was obtained as a pale yellow oil, (S)-methyl 2-((tertbutoxycarbonyl)amino)-3-(3,5-dichloro-4-fluorophenyl)propanoate, 0.102 g which was taken into next stepdirectly.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17318-08-0, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; Miller, Michael Matthew; Mapelli, Claudio; Allen, Martin Patrick; Bowsher, Michael S.; Boy, Kenneth M.; Gillis, Eric P.; Langley, David R.; Mull, Eric; Poirier, Maude A.; Sanghvi, Nishith; Sun, Li-Qiang; Tenney, Daniel J.; Yeung, Kap-Sun; Zhu, Juliang; Reid, Patrick C.; Scola, Paul Michael; (892 pag.)US9308236; (2016); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

17318-08-0, The chemical industry reduces the impact on the environment during synthesis 17318-08-0, name is 5-Bromo-1,3-dichloro-2-fluorobenzene, I believe this compound will play a more active role in future production and life.

A stirred mixture of 5-bromo-1,3-dichloro-2-fluorobenzene (2.00 g, 8.20 mmol), l-methoxy-4-vinylbenzene (1.32 g, 9.80 mmol), and triethylamine (20 mL) under argon was degassed for 5 minutes. Palladium(II) acetate (0.0368 g, 0.164 mmol) and 1,1′- bis(diphenylphosphino)ferrocene (0.181 g, 0.328 mmol) were added and the reaction was heated to 90 C for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography provided the title compound as an off-white solid (1.60 g, 67%): lH NMR (300 MHz, CDCb) delta 7.41 (d, J = 8.8 Hz, 2H), 7.31 (s, 1H), 7.37 (s, 1H), 6.96 (d, J = 16.0 Hz, 1H), 6.89 (d, J = 8.8 Hz, 2H), 6.76 (d, J = 16.0 Hz, 1H), 3.84 (s, 3H); ESIMS m/z 297 ([M + H]+).

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

Reference:
Patent; DOW AGROSCIENCES LLC; HEEMSTRA, Ronald J.; ROSS, Ronald; DEKORVER, Kyle A.; GRAY, Kaitlyn; KNUEPPEL, Daniel I.; VEDNOR, Peter; MARTIN, Timothy P.; ECKELBARGER, Joseph D.; DAEUBLE, John F.; HUNTER, Ricky; DEMETER, David A.; TRULLINGER, Tony K.; BAUM, Erich W.; BENKO, Zoltan L.; CHOY, Nakyen; CROUSE, Gary D.; LI, Fangzheng; NISSEN, Jeffrey; OLSON, Monica B.; RIENER, Michelle; SPARKS, Thomas C.; WESSELS, Frank J.; YAP, Maurice C.; (981 pag.)WO2016/168059; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics