Hydrogen Bromide → HCID 57572811, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL flask containing 6-propylnonan-1-ol (4,92 g, 26,4 mmol) was added hydrobromic acid 48% (12 mL, 105,6 mmol, 4 eq.) and conc. sulfuric acid (1,4 mL, 26,4 mmol, 1 eq.) and the mixture was heated to reflux (95 ° C.) for 14 h. The reaction was cooled to room temperature before adding H2O (40 mL). The mixture was extracted with dichloromethane (3×120 mL) and the combined organic phases were washed with aqueous sodium bicarbonate (40 mL, 1 M). Drying over magnesium sulfate and evaporation gave 1-bromo-6-propylnonane (5,87 g, 89% yield) as a brown liquid. 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,40 (t, J=6,8 Hz, 2H); 1,86 (tt, J=6,8 Hz, J=6,8 Hz, 2H); 1,45-1,35 (m, 2H); 1,34-1,15 (m, 13H); 0,88 (t, J=6,8 Hz, 6H). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 36,9; 36,0 (2C); 34,0; 33,5; 33,9; 28,7; 25,8; 19,8 (2C); 14,5 (2C).

Provenance & Evidence