Chemical Properties
colorless or pale yellow liquid. soluble in acetone, benzene and chloroform. intermediates for organic synthesis.
Uses
1-Bromotetradecane was used in the synthesis of tetradecylferrocene, cationic and zwitterionic gemini surfactants, and 9-tetradecylcarbazole. Also used for synthesis of metallomesogenic polymers based on bis[η1(N)-3,4-dialkyloxybenzylidene-4-dodecyloxyaniline]dichloropalladium(II) with octyl, decyl, dodecyl, tetradecyl and hexadecyl alkyl groups.
Preparation
1-Bromotetradecane is synthesized from 1-tetradecanol by bromination. The 1-tetradecanol was added to the reaction pot, and the sulfuric acid was added dropwise with stirring, and the stirring was continued for half an hour after the addition. Then add hydrobromic acid, heat to 99-101°C, and react for 8h. Cool to 30°C, stop stirring, stand for 12 hours, and separate the upper layer of oil, and adjust the pH to 8 with 10% sodium carbonate solution. The water layer was separated, the oily substance was washed twice with an equal volume of 50% ethanol, the washed oily substance was added with sodium carbonate, stirred intermittently, and dried for 24h. Filtration to obtain 1-bromotetradecane.
Synthesis
General procedure for the synthesis of bromotetradecane from 1-tetradecene: 1-tetradecene (393 mg, 2 mmol) was dissolved in hexane (2 mL) at room temperature, followed by the addition of 1c (17 wt%, 1.3 g, 2.7 mmol). The reaction mixture was stirred for 1 h at room temperature. Upon completion of the reaction, the reaction was quenched with deionized water (10 mL) and extracted with ether (10 mL × 3). The organic phases were combined, washed with saturated saline (15 mL × 2), dried over anhydrous sodium sulfate (5 g), and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using hexane as eluent to afford bromotetradecane (543 mg, 98% yield) as a colorless liquid. The structure of the product was confirmed by 1H-NMR (500 MHz, CDCl3) and 13C NMR (126 MHz, CDCl3): 1H-NMR δ 0.89 (t, J = 6.9 Hz, 3H), 1.26-1.31 (m, 18H), 1.84 (dd, J = 7.7 Hz, J = 6.7 Hz, 2H), 3.41 (t, J = 6.9 Hz, 2H); 13C NMR δ 14.21, 22.85, 28.38, 28.97, 29.55, 29.64, 29.74, 29.85 (4C), 32.11, 33.03, 33.59.
References
[1] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1190 - 1193
[2] Synlett, 2010, # 13, p. 2014 - 2018
