1-(4-Bromophenyl)hexane synthesis
- Product Name:1-(4-Bromophenyl)hexane
- CAS Number:23703-22-2
- Molecular formula:C12H17Br
- Molecular Weight:241.17
1746-28-7
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693-04-9
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23703-22-2
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Yield:23703-22-2 94 %Chromat.
Reaction Conditions:
with cobalt(II) chloride;lithium iodide;isoprene in tetrahydrofuran at -78 - 50; for 5 h;Inert atmosphere;
Steps:
1-Bromo-4-hexylbenzene (5rj)
General procedure: Coupling of Alkyl Halides with t-BuMgCl; Procedure 1 (P1)An alkyl halide (1.0 mmol), decane (63 mg as an internal standard)and LiI (5.3 mg, 0.04 mmol) were added to a dry, nitrogen-flushedtest tube equipped with a rubber septum and a magnetic stir bar.THF (0.8 mL) was added and the solution was cooled to -78 °C usinga dry ice/EtOH bath. t-BuMgCl (2a) (1.5 mL, 0.81 M in THF,1.2 mmol) was added slowly followed by isoprene (136.2 mg, 2.0mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as apowder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2should be added after isoprene, otherwise the catalytic performancedecreases significantly). The cold bath was removed and the mixturewas warmed to r.t. (ca. over 10 min), and then heated for 5 h bysuspending the reaction vessel in an oil bath kept at 50 °C. (Note 2:when the reaction mixture was heated at 30 °C during this stage, unidentifiedside reactions occurred resulting in low yields of couplingproducts). The resulting mixture was cooled to 0 °C in an ice bathand the reaction was quenched with aq HCl (5 mL, 1 M). The productwas extracted with Et2O (3 × 20 mL). The combined organiclayer dried over Na2SO4, concentrated and analyzed by gas chromatographyto determine the GC yield. The residue was purified by silicagel column chromatography or by GPC. 1.0 mmol) and n-BuMgCl (2j) (1.0 M in THF, 1.2 mmol) were reactedunder standard conditions.Yield: 94% (determined by GC using decane as an internal standard).
References:
Iwasaki, Takanori;Takagawa, Hiroaki;Okamoto, Kanako;Singh, Surya Prakash;Kuniyasu, Hitoshi;Kambe, Nobuaki [Synthesis,2014,vol. 46,# 12,art. no. SS-2014-Z0096-PSP,p. 1583 - 1592]
7295-46-7
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23703-22-2
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76287-58-6
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23703-22-2
174 suppliers
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