1,6-Dibromohexane → HCID 67540595, compound

Participants

Reaction Steps

A suspension of 37 (7.13 g, 41.22 mmol) and NaOH (1.52 g, 38.10 mmol) in acetonitrile (309 ml) was stirred under reflux for 1 h before 1,6-dibromohexane (2.51 g, 10.31 mmol) was added in one portion. The reaction mixture was stirred under reflux for another 22 hours before the precipitates were removed by filtration. The filtrate was quenched with water and extracted with methylene chloride. The extracts were combined, washed with water and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by gradient column chromatography on silica gel with hexanes/ethyl acetate 19:1 to 9:1 (v/v) as the eluent to yield 38 (4.02 g, 91%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 7.15-7.11 (m, 2H), 7.07-7.04 (m, 4H), 6.83-6.80 (m, 2H), 3.96-3.93 (t, 4H), 1.82-1.79 (t, 4H), 1.55-1.51 (m, 4H).

Provenance & Evidence