Synthetic Route of 33863-76-2, 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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.
To a degassed solution of (R)-3-((R)-3-Amino-2-oxo-perhydro- azepin-l-yl)-piperidine-l -carboxylic acid tert-butyl ester 39.6 (0.6 g, 1.9 mmol) in toluene (40 mL) was added sodium tert-butoxide (0.34 g, 3.6 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)- Iota , -binaphthyl (0.20 g, 0.33 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.1 1 g, 0.12 mmol) and l-Bromo-3-chloro-5-fluoro-benzene (0.5 g, 2.4 mmol). The solution was purged under an atmosphere of argon and heated to reflux for 2.5 h. The reaction was cooled to room temperature, filtered through celite pad, diluted with ether and washed with a solution of NaHC03, brine, dried(Na2SC>4) filtered and solvent was concentrated in vacuo to afford a residue which purified by flash chromatography (gradient DCM/MeOH, 0 to 5%) to afford 0.4g, 48.2%. LCMS m z 385.4 [M – tBu]+.
The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chloro-5-fluorobenzene. I believe this compound will play a more active role in future production and life.
Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
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