Application of iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds
A technology of di-tert-butyl imidazolium and aryl benzyl ether, which is applied in the field of preparation of organic compounds to achieve good catalytic activity, clear structure, and good atom economy
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Embodiment 1
[0029] Embodiment one: containing 1,3-di-tert-butylimidazolium cation (molecular formula is [( t BuNCH=CHN t Bu)CH][FeBr 4 ]) synthesis of iron(III) complexes
[0030] 1,3-Di-tert-butyl imidazolium bromide (0.26 g, 1.0 mmol) was added to a THF solution of ferric tribromide (0.27 g, 0.9 mmol), 60 oC The reaction was carried out under vacuum for 24 hours, the solvent was removed in vacuo, washed with hexane, drained, extracted with tetrahydrofuran, and the supernatant liquid was transferred by centrifugation. Hexane was added to the supernatant liquid for recrystallization, and a reddish-brown solid powder was precipitated at room temperature, with a yield of 91%.
[0031] The chemical structural formula is as follows:
[0032]
[0033] Carry out elemental analysis to product, the result is as follows:
[0034]
[0035] Since the iron complex is paramagnetic, it was not characterized by NMR.
[0036] Complex [( t BuNCH=CHN t Bu)CH][FeBr 4 ] exists in the form of io...
Embodiment 2
[0039] Embodiment two: [( t BuNCH=CHN t Bu)CH][FeBr 4 ] catalyzed oxidative coupling reaction of 4-nitrophenol with toluene
[0040] Add 4-nitrophenol (69.5 mg, 0.5 mmol), catalyst (28 mg, 0.05 mmol), di-tert-butyl peroxide (140 μl, 0.75 mmol), toluene (4.5 ml ), at 130 oC for 24 hours, after the reaction was cooled to room temperature, the product was purified by column chromatography (with a mixed solvent of ethyl acetate / petroleum ether volume ratio of 1:10 as the developing solvent), and the yield was 89%.
[0041] Dissolve the product in CDCl 3 Medium (about 0.4 mL), seal the tube, measure and characterize on a Unity Inova-400 NMR instrument at room temperature: 1 H NMR (400 MHz, CDCl 3 , TMS): 8.29 - 8.17 (m, 2H), 7.48 - 7.37 (m, 5H),7.08 -7.00 (m, 2H), 5.19 (s, 2H).
[0042] The product is p-nitrophenylbenzyl ether:
[0043]
[0044] The above-mentioned iron catalyst was replaced with 20 mol% copper powder, and other conditions were unchanged, and the target ...
Embodiment 3
[0045] Embodiment three: [( t BuNCH=CHN t Bu)CH][FeBr 4 ] catalyzed oxidative coupling reaction of 4-trifluoromethylphenol with toluene
[0046] Add 4-trifluoromethylphenol (81.05 mg, 0.5 mmol), catalyst (28 mg, 0.05 mmol), di-tert-butyl peroxide (140 microliters, 0.75 mmol) and toluene ( 4.5 ml) at 130 o The reaction was carried out at C for 24 hours, cooled to room temperature after the reaction, and the product was purified by column chromatography (petroleum ether was used as developing agent), and the yield was 86%.
[0047] Dissolve the product in CDCl 3 Medium (about 0.4 mL), seal the tube, measure and characterize on a Unity Inova-400 NMR instrument at room temperature: 1 H NMR (400 MHz, CDCl 3 , TMS): 7.53 (d, J = 8.7 Hz, 2H), 7.45 - 7.30 (m,5H), 7.01 (d, J = 8.7 Hz, 2H), 5.08 (s, 2H).
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