white to off-white powder and chunk
4-Phenoxyphenylboronic acid can be used as a reactant:
- In the Suzuki-Miyaura coupling reaction to synthesize aryl derivatives via C-C bond formation by reacting with different aryl halides over a palladium catalyst.
- To prepare 1-phenoxy-4-(trifluoromethyl)benzene via oxidative trifluoromethylation using Chan-Lam-type reaction conditions.
- To synthesize evobrutinib, a potent Bruton′s tyrosine kinase (BTK) inhibitor.
4-Phenoxybenzeneboronic Acid is an intermediate used to prepare biphenyl derivatives of nitotrifluoromethoxybenzyloxydihydroimidazooxazines with antitubercular activity. It is also used in the synthesis of pyrrolo pyrimidines as potent inhibitors of Lck kinase.
4-Bromodiphenyl ether (100 g, 0.402 mol)Was dissolved in anhydrous THF (800 mL)Under nitrogen protection,Cooled to -78 ° C,N-butyllithium (n-BuLi) (177 mL, 0.442 mol)The temperature is kept below -65 ° C,After stirring for 1 h,Continue to maintain the temperature -60 ,Triisopropyl borate (90 g, 0.482 mol) was added dropwise,Slowly rose to 0 ° C, stir for 3 h.Water (300 mL) was added under ice bath overnight. The reaction solution was concentrated to remove the organic phase,With 12N concentrated hydrochloric acid pH adjusted to 1 ~ 2,Precipitation of solids,Filtration and drying gave 4-phenoxyphenylboronic acid (77 g, yield 90%).
[1] Patent: CN106146511, 2016, A. Location in patent: Paragraph 0147; 0148; 0149
[2] Organic Process Research and Development, 2018, vol. 22, # 6, p. 741 - 746
[3] Patent: US2002/156081, 2002, A1
[4] Patent: US6921763, 2005, B2
