ChemicalBook CAS DataBase List 1-Bromotetradecane

1-Bromotetradecane synthesis

4synthesis methods

Product Name:1-Bromotetradecane
CAS Number:112-71-0
Molecular formula:C14H29Br
Molecular Weight:277.28

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.

1120-36-1
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112-71-0
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Yield:112-71-0 98%

Reaction Conditions:

with hydrogen bromide in 1,4-dioxane;hexane at 20; for 1 h;

Steps:

Typical procedure for bromination of 1-tetradodecene with HBr/1,4-dioxane (1c) (Table 3 Entry 1)
To a mixture of tetradecene (393 mg, 2 mmol) in hexane (2 mL), was added 1c (17 wt%, 1.3 g,2.7 mmol) at room temperature. The mixture was then stirred for 1 h. The resulting mixture was quenched with water (10 mL) and extracted with diethyl ether (10 mL × 3). The combined organic extract was washed with brine (15 mL × 2) and then dried over Na2SO4 (5 g) and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (eluent: hexane) to afford bromotetradecane (543 mg, 98%) as a colourless liquid. 1H-NMR (500 MHz, CDCl3) 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 (126 MHz, CDCl3) 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:

Nishio, Yuya;Mifune, Ryota;Sato, Taisuke;Ishikawa, Shin-ich;Matsubara, Hiroshi [Tetrahedron Letters,2017,vol. 58,# 12,p. 1190 - 1193] Location in patent:supporting information

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1120-36-1
176 suppliers
$15.00/25mL

112-71-0
320 suppliers
$5.00/10g