Some tips on Aminoferrocene

The chemical industry reduces the impact on the environment during synthesis,1273-82-1,Aminoferrocene,I believe this compound will play a more active role in future production and life.

1273-82-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Aminoferrocene, cas is 1273-82-1,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.

Aminoferrocene (0.40 g, 1.98 mmol) and acetaldehyde (0.1 mL, 1.98 mmol) were dissolved on methanol (10 mL) and refluxed for 2 h. Then, Na[B(CN)H3] (0.12 g, 1.98 mmol) dissolved in MeOH (10 mL) was slowly added. The mixture obtained was acidified with HCl (2 mL, 1 M in water) and left stirring for 30 min. Afterwards, the solvent was removed in vacuum (0.01 mbar) and the rest was mixed with triphosgene (0.59 g, 1.98 mmol) in toluene (25 mL). The suspension obtained was refluxed for 1 h, cooled down to 22C and then mixed with solution of 4-(hydroxymethyl)phenylboronic acid pinacol ester (0.46 g, 1.98 mmol) in toluene (10 mL). The resulting solution was heated to 120C and stirred at these conditions for 6 h. Then, the solvent was removed in vacuum (0.01 mbar) and the crude product was purified by column chromatography on silica gel using hexane containing 5% of acetone as eluent. Yield 0.20 g (20%). Rf= 0.5 (silica, eluent – hexane / acetone, 5/1, v/v). 1H NMR (400 MHz, acetone-d6), delta in ppm: 1.27 (t, 3H), 1.33 (s, 12H), 3.77 (q, 2H), 4.00 (s, 2H), 4.13 (s, 5H), 4.53 (m, 2H), 5.22 (s, 2H), 7.46 (d, 1 H), 7.77 (d, 2H). 13C NMR (100.55 MHz, acetone-d6), delta in ppm: 14.4, 25.3, 45.8, 62.8, 65.1, 66.9, 67.5, 69.8, 84.6, 127.8, 128.1, 135.7 (two overlapping peaks), 139.1, 141.2. FAB MS: calculated for C26H32BNO4Fe 489.2, found 489.2 m/z. C, H, N analysis: calculated for C26H32BNO4Fe – C 63.8%; H 6.6%; N 2.9%; found – C 63.8%; H 6.8%; N 2.9%. IR spectra (in KBr), wave number in cm-1: 3101, 2973, 1696, 1623.

The chemical industry reduces the impact on the environment during synthesis,1273-82-1,Aminoferrocene,I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ruprecht-Karls-Universitaet Heidelberg; EP2497775; (2012); A1;,
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