Hexane → HCID 22398285, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 mL one necked round bottom flask, 3,3,6-trimethylindan-5-ol was dissolved in acetic acid (10 mL). The solution was cooled down to 0° C. followed by slow addition of bromine (290 μL, 5.65 mmol). The reaction was slowly warmed up to room temperature. After 3 h of stirring, the reaction was completed. Excess acetic acid was removed by rotavap, and the residue was quenched with ascorbic acid solution. The content was extracted with sodium bicarbonate and brine. Plugged column with silica gel 5:95 ethyl acetate:hexane gave colorless oil, 4-bromo-3,3,6-trimethylindan-5-ol (82% yield). 1H NMR (300 MHz, CDCl3): δ 1.42 (s, 6H), 1.98(dd, 2H, J=15.11, 7.55 Hz), 2.24 (s, 3H), 2.54 (s, 3H), 2.57 (s, 3H), 2.85(d, 2H, J=7.55 Hz), 3.89 (s, 3H), 5.12(d, 1H, J=3.40 Hz), 6.31 (s, 1H), 6.95(m, 1H), 7.01 (s, 1H), 7.12(d, 1H, J=3.40) 8.34 (bs, 1H).

Provenance & Evidence