Synthetic Route of C20H12Br2O2. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol, is researched, Molecular C20H12Br2O2, CAS is 119707-74-3, about Discrimination of remote chirality of primary alcohols using 1,1′-binaphthyl-2,2′-diyl phosphoroselenoyl chlorides as a chiral molecular tool. Author is Murai, Toshiaki; Itoh, Hikaru.
The reaction of trichlorophosphine, 1,1′-binaphthyl-2,2′-diols with various substituents at the 3,3′-positions, and elemental selenium in the presence of Et3N gave phosphoroselenoyl chlorides in low to high yields depending on the substituents on the binaphthols. To evaluate their utility as chiral derivatizing agents of primary alcs. having a chiral center β to the hydroxy group, the obtained chlorides were reacted with alcs. to yield phosphoroselenoic acid esters. 31P and 77Se NMR spectra of some esters with an unsubstituted binaphthyl group showed two signals corresponding to their diastereomers. Among them, the diastereomers of alcs. with chiral quaternary centers were clearly distinguished in the NMR spectra. This discrimination was further improved by the use of esters having binaphthyl groups with substituents at the 3,3′-positions. In particular, the signals due to the diastereomers of esters having binaphthyl groups with C6H4C6H3Me2-3,5 and SiiPr3 groups were more clearly separated in NMR spectra. Sequential recrystallization of the esters derived from primary alcs. having quaternary carbon centers gave only one of the diastereomers. Their mol. structures were determined by X-ray analyses.
Different reactions of this compound((S)-3,3′-Dibromo-1,1′-bi-2-naphthol)Synthetic Route of C20H12Br2O2 require different conditions, so the reaction conditions are very important.
Reference:
Bromide – Wikipedia,
bromide – Wiktionary