Efficient synthesis of 6-mono-bromo-1,1′-bi-2-naphthol
✍ Scribed by Dongwei Cai; Robert D Larsen; Paul J Reider
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 73 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Through mono-ester formation of 1,1%-bi-2-naphthol (BINOL) with pivaloyl chloride the selective mono-bromination was achieved cleanly on the other ring to afford 6-mono-bromo-1,1%-bi-2-naphthol in an efficient 86% yield.
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
In the title compound, C~18~H~29~BrN~4~, both piperazine rings assume a chair conformation. Weak intermolecular C—H...Br interactions result in dimeric associations in the crystal structure. There are no further interactions between neighbouring dimer units.
Racemic forms of 1,1 0 -bi-(2-naphthol) (BINOL) monopivalate (rac-1) and its 6-nitro substitute (rac-2) were structurally characterized by X-ray crystallography. Molecules of opposite chirality form dimers in the crystalline state of rac-1 through OAHÁ Á ÁO hydrogen-bonds between the free hydroxy an