Sodium Hydroxide → 4-Bromo-1-indan-5-yloxybutane

Participants

Reaction Steps

5-Indanol (1 g, 7.45 mmol) in NaOH(aq) (5.22 mL, 20.88 mmol, 4 M soln.) was treated with dibromobutane (3.38 mL, 28.3 mmol) and t-butylammoniumhydrogensulfate (catalytic). The solution was placed in a Robbins™ oven for 14 hours at 99° C. Upon cooling, the pH was adjusted to ˜8 with 4 N NaOH. CH2Cl2 was then added and the solution washed with H2O (×2) and brine. The organic layer was dried over MgSO4 and concentrated to an oil. The oil was then dissolved in 4:1 hexane/EtOAc and passed through a plug of silica gel which was then washed with 4:1 hexane/EtOAc. The filtrate was concentrated to afford 4-bromo-1-indan-5-yloxybutane.

Provenance & Evidence