Hydrochloric Acid → HCID 22252946, compound

Temperature

0 °C

To a stirred mixture of 5,6,7,8-tetrahydronaphthalen-1-ol (29.2 g, 195 mmol) in dichloromethane (300 mL) was added diisopropylamine (2.75 mL, 19.5 mmol) at room temperature. The reaction mixture was cooled to 0° C., and N-bromosuccinimide (36.62 g, 205 mmol) dissolved in dichloromethane (1.0 L) was added dropwise over 6.5 h. The mixture was then allowed to stir at room temperature for an additional 1 h. At this point 1N HCl was slowly added until the mixture reached pH 1, added H2O (100 mL), separated the dichloromethane solvent layer, dried the organic extracts over anhydrous sodium sulfate, and filtered. Concentrated the filtrate in vacuo at ambient temperature to produce a clear oil, added hexane (1.0 L) to precipitate unreacted N-bromosuccinimide, collected the resulting precipitate and washed with hexane. The filtrate was concentrated in vacuo, and the resultant oil purified by column chromatography on silica gel (elution with 2.5% ethyl acetate/hexane) to afford 32.3 g (73%) of the title compound of 2-bromo-5,6,7,8-tetrahydronaphthalen-1-ol as an off-white solid (MW 227.10, C10H11BrO).

1. additionwas added dropwise over 6.5 h
2. customseparated the dichloromethane solvent layer
3. dry with materialdried the organic extracts over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationConcentrated the filtrate in vacuo at ambient temperature
6. customto produce a clear oil
7. customto precipitate unreacted N-bromosuccinimide
8. customcollected the resulting precipitate
9. washwashed with hexane
10. concentrationThe filtrate was concentrated in vacuo
11. customthe resultant oil purified by column chromatography on silica gel (elution with 2.5% ethyl acetate/hexane)

ORD record

ord-faa95117e62841fdbbbc33dfaec0a26b

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06992100B2