10-BROMO-1-DECENE

A round-bottomed flask was charged with 9-decen-1-ol 3 (10.0 g, 64.1 mmol)and CHFor synthesis of 1-bromo-9-decene (2), 9-decen-1-ol (1, 0.506 g 3.24 mmol, Sigma-Aldrich, St. Louis, MO) was dissolved in 10 mL of CHTo a solution of dec-9-en-1-ol (1.22 g, 7.82 mmol) in DMF (18 ML) was added triphenylphosphine (2.30 g, 8.77 mmol).The solution was cooled to 0° C. and NBS (1.52 g, 8.54 mmol) was added in portions.After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.8 ML).The solution was diluted with ether (80 ML), washed with water, saturated aqueous NaHCO3 and brine successively.The organic layer was dried and concentrated.The residue was purified by flash chromatography on silica gel, eluding with hexane to afford 10-bromo-dec-1-ene (1.38 g, 81percent) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.80 (1H, m), 4.94 (2H, m), 3.38 (2H, t, J=6.9 Hz), 2.02 (2H, m), 1.83 (2H, m), 1.20-1.55 (10H, m); 13C NMR (75 MHz, CDCl3) δ 139.17, 114.30, 34.29, 34.02, 33.06, 29.53, 29.25, 29.12, 28.96, 28.40. First, 24.67 g (0.15 M) of 9-decene-1ol (compound (20)) was dissolved in 180 mL of diethyl ether. General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product.

Molecular Weight:219.16
XLogP3:5.5
Rotatable Bond Count:8
Exact Mass:218.06701
Monoisotopic Mass:218.06701
Heavy Atom Count:11
Complexity:78.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes