1-Bromodecane synthesis
- Product Name:1-Bromodecane
- CAS Number:112-29-8
- Molecular formula:C10H21Br
- Molecular Weight:221.18
77899-13-9
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112-29-8
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Yield:112-29-8 95.5%
Reaction Conditions:
with sodium tetrahydroborate;hydrogen;nickel diacetate;zinc(II) oxide in isopropyl alcohol at 35 - 55; for 6 h;
Steps:
16 Example 16
Nickel(II) acetate (1.34 g, 0.0054 mol), zinc(II) oxide (0.44 g, 0.0054 mol), and 2-propanol (38.3 g, 0.64 mol) were placed in a reactor, heated at 50 to 55° C., and stirred for 1 hour. Next, the mixture was cooled to 40° C., subjected to addition of sodium borohydride (0.26 g, 0.0069 mol), and stirred at 35 to 45° C. for 2 hours. Subsequently, (4Z)-1-bromo-4-decene (comp. of Formula 1) (96.9 g, 0.44 mol) was added into the reactor in which the NiZn catalyst had been prepared, then the mixture was warmed to 40 to 50° C., and hydrogen gas was fed thereto for 6 hours while the progress of the reaction was observed. The resulting mixture was cooled to 40° C. or less, and the NiZn catalyst was filtered off, then water (14.6 g) was added to the filtrate for liquid separation. The organic phase was concentrated under reduced pressure, and then the residue was subjected to vacuum distillation to obtain 1-bromodecane (comp. of Formula 2) (93.4 g, 0.42 mol) at a yield of 95.5%. The yield of decane, which was a dehalogenation product, was 3.0%, so that the by-product was only slightly yielded. 1-bromodecane (comp. of Formula 2) [Nuclear magnetic resonance spectrum] 1H-NMR (500 MHz, CDCl3): δ=0.88 (3H, t, J=7.1 Hz), 1.22-1.34 (12H, m), 1.38-1.45 (2H, m), 1.85 (2H, quint-like, J=7.3 Hz), 3.40 (2H, t, J=6.9 Hz); 13C-NMR (125 MHz, CDCl3): δ=14.10, 22.67, 28.17, 28.76, 29.28, 29.44, 29.50, 31.86, 32.84, 34.05 [Mass spectrum] EI-mass spectrum (70 eV): m/z 220 (M+), 149, 135, 121, 99, 85, 69, 57, 43, 29 [Infrared absorption spectrum] (NaCl): v=2957, 2925, 2854, 1465, 647, 564
References:
US2019/322607,2019,A1 Location in patent:Paragraph 0178; 0179; 0180; 0181; 0182; 0183
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