Hydrochloric Acid → 5-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

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Reaction Conditions

Reaction Steps

A 500 mL three-necked flask fitted with an addition funnel, reflux condenser and thermometer was charged with aluminum chloride (33.34 g, 250 mmol) and heated to 75-80° C. 1-Tetralone (14.6 g, 13.3 mL, 100 mmol) was added dropwise over 10 min. The resulting brown slurry was stirred for 3 min before dropwise addition of bromine (19.21 g, 6.15 ml, 120 mmol) over 15 min. The mixture was stirred for 5 min and then poured into a mixture of ice (300 g) and 12N HCl (40 mL). The mixture was stirred until the aluminum chloride was dissolved and then diluted with water (200 mL). The mixture was extracted with diethyl ether (3×300 mL) and the combined organics were washed with water (2×300 mL), dried (sodium sulfate), filtered and evaporated in vacuo to give a dark brown mixture of 5- and 7-bromo-1-tetralone. The isomers were separated using silica gel flash chromatography (Biotage Flash 75, elution solvent 20/1 hexanes:MTBE) to yield 5-bromo-1-tetralone (11.59 g, 51%) and 7-bromo-1-tetralone (9.45 g, 42%).

Provenance & Evidence