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
693-04-9
23703-22-2
General procedure for the synthesis of 1-bromo-4-(2-bromoethyl)benzene with n-butylmagnesium chloride as a raw material for the synthesis of 1-bromo-4-hexylbenzene: coupling reaction of alkyl halides with t-BuMgCl. Step 1 (P1): alkyl halides (1.0 mmol), decane (63 mg, as an internal standard) and LiI (5.3 mg, 0.04 mmol) were added to a reaction tube equipped with a rubber septum and a magnetic stirrer under a dry nitrogen atmosphere. THF (0.8 mL) was then added and the solution was cooled to -78 °C using a dry ice/EtOH bath. Slowly t-BuMgCl(2a) (1.5 mL, 0.81 M of THF solution, 1.2 mmol) was added, followed by isoprene (136.2 mg, 2.0 mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as a powder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2 should be added immediately after isoprene addition or the catalytic efficiency will be significantly reduced.) Remove the cold bath, warm the mixture slowly to room temperature (about 10 min), and then heat the reaction vessel in a 50°C oil bath for 5 hr. (Note 2: If the reaction mixture is heated at 30 °C at this stage, unidentified side reactions can occur, resulting in lower yields of coupling products.) Upon completion of the reaction, the mixture is cooled to 0 °C in an ice bath and the reaction is quenched with 1 M aqueous HCl (5 mL). The product was extracted with Et2O (3 x 20 mL). The organic layers were combined, dried with Na2SO4, concentrated and analyzed by gas chromatography to determine the GC yield. The residue was purified by silica gel column chromatography or GPC. Under standard conditions, 1.0 mmol of 1-bromo-4-(2-bromoethyl)benzene was reacted with n-BuMgCl(2j) (1.0 M in THF, 1.2 mmol) in 94% yield (determined by GC using decane as an internal standard).
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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23703-22-2
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