1-Bromooctane → 1-Azidooctane

In a 100 mL round bottomed flask, sodium azide (2.60 g, 37.6 mmol) was dissolved in 80 mL DMSO, 1-Octyl bromide (5.5 g, 28.4 mmol) was added and stirred at room temperature for 5 h. The reaction was quenched by addition of water (200 mL) and was stirred for 1 h. The mixture was extracted with diethyl ether (50×3). The combined organic layers were washed with brine solution. The ether solution was dried over anhydrous MgSO4 and the solvent was removed by rotary evaporation. The product was further purified by filtration through a short silica gel column using hexane as eluent. Yield: 2.5 g (78%) IR (neat) 2957, 2857, 2093, 1466, 1377, 1279 cm−1; 1H NMR (400 MHz, CDCl3) δ 3.21 (d, J=6.2 Hz, 2H), 1.55-1.57 (m, 2H), 1.25-1.32 (m, 10H), 0.84 (m, 3H); 13C NMR (CDCl3) δ 51.51, 31.80, 29.19, 29.16, 28.89, 26.77, 22.66, 14.06,

1. customThe reaction was quenched by addition of water (200 mL)
2. stirringwas stirred for 1 h
3. extractionThe mixture was extracted with diethyl ether (50×3)
4. washThe combined organic layers were washed with brine solution
5. dry with materialThe ether solution was dried over anhydrous MgSO4
6. customthe solvent was removed by rotary evaporation
7. filtrationThe product was further purified by filtration through a short silica gel column

ORD record

ord-1dac48283c014cea99e7af9d1eedbef7

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772048B2