Hydrochloric Acid → HCID 22252946, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence