Category: 1798-85-2

Application of 1798-85-2,Some common heterocyclic compound, 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene, molecular formula is C9H9Br, 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 stirred suspension oflntermediate B-4 (201.8 mg, 0.647 mmol), 1-bromo-3-cyclopropylbenzene (246.7 mg, 1.252 mmol), Pd2(dba)3 (58.5 mg, 0.064 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (“X-Phos”) (30.7 mg, 0.064 mmol)and potassium carbonate (414.7 mg, 3.00 mmol) in t-BuOH (4.0 mL) was degassed(pump/N2 x 3) and then heated to 80 oc overnight. The reaction mixture was cooled to20 room temperature. The mixture was diluted with EtOAc, filtered through a 4 )lmmembrane filter, concentrated, and then dried under vacuum. The residue was purifiedby flash chromatography (Teledyne ISCO CombiFlash Rf, gradient ofO% to 100% using solvent A/B=heptane/EtOAc over 15 column volumes, REDISEP Si02 40g, loaded asDCM solution). Obtained Intermediate B-12A (134.0 mg, 48%) as a tan solid: HPLC_RT=2.218 min (Waters SunFire C18 2.1x30mm, MeOH/H20/0.1% TFA, 2min gradient,wavelength= 254 nm); MS(ES): m/z= 372/374 [M-t-Bu+ It; 1H NMR (400 MHz,5 chloroform-d) 8 7.05-7.15 (m, IH), 6.59 (d, J=7.70 Hz, IH), 6.47-6.55 (m, 2H), 5.61 (d,J=7.26 Hz, IH), 4.53-4.65 (m, IH), 4.26-4.33 (m, IH), 3.66 (dd, J=9.57, 11.77 Hz, IH),1.75-1.85 (m, IH), 1.46 (s, 9H), 0.85-0.97 (m, 2H), 0.57-0.71 (m, 2H).

The synthetic route of 1798-85-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILL, Patrice; QUESNELLE, Claude A.; SAULNIER, Mark G.; GAVAI, Ashvinikumar V.; WO2014/47369; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1798-85-2, 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. 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A Schlenk flask was charged with an appropriate amount of complex 2b (0.016mmol, 2.0mol%) and the corresponding bromo or iodo arene (0.77mmol). The flask was cycled with nitrogen and vacuum. Afterwards a THF solution of benzylzinc bromide (2.2mL, 1.1mmol, 0.5M in THF) was added. The flask was sealed and heated at 70C for 24h. After that time, the mixture was cooled, and dichloromethane and water were added. The aqueous layer was extracted with dichloromethane and the collected organic layers were washed with water and dried with Na2SO4. The coupling product was confirmed by GC-MS (with n-dodecane as internal standard) and NMR analysis. The analytical properties of the products are in agreement with literature data [6a,24].

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

Reference:
Article; Someya, Chika I.; Irran, Elisabeth; Enthaler, Stephan; Inorganica Chimica Acta; vol. 421; (2014); p. 136 – 144;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene, molecular formula is C9H9Br, 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. COA of Formula: C9H9Br

A mixture of N- (4- (methylsulfonyl ) benzyl) -3, 4-dihydro-2H- (3811) 1 , 4-benzoxazine-7-carboxamide (0.028 g, 0.08 mmol), l-bromo-3- cyclopropylbenzene (32 mg, 0.160 mmol), RuPhos Pd Gl (5.83 mg, 8.00 mumol) , RuPhos (3.73 mg, 8.00 muiotatauiotaomicron) , NaOtBu (0.023 g, 0.240 mmol) and DME (1 mL) was heated at 130 C for 2 h under (3812) microwave irradiation. The reaction mixture was diluted with AcOEt (3 mL) and quenched with H20 (1 mL) , and stirred for 2 min. The organic layer was separated and then the aqueous layer was extracted with EtOAc (2 mL) . The combined organic layer was evaporated by blowing away with the air at 60 C. The residue was purified by preparative HPLC (Actus Triart C18, eluted with MeCN/10 mM NH4HCO3 aq. 5:95?100:0). Pure fractions were combined and concentxated by blowing away with the air at 60C to afford the title compound (19.8 mg, 0.0428 mmol, 54%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1798-85-2, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; SHIOKAWA, Zenyu; YUKAWA, Tomoya; IMADA, Takashi; NEGORO, Nobuyuki; ODA, Tsuneo; SASAKI, Satoshi; NARA, Yoshi; SUZUKI, Shinkichi; SATO, Ayumu; ISHII, Naoki; SHIBUYA, Akito; NAKAGAWA, Yasuo; COLE, Derek; GIBSON, Tony; IVETAC, Anthony; SWANN, Steve; TYHONAS, John; (472 pag.)WO2018/30550; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary