Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 52997-43-0, name is 7-(Bromomethyl)pentadecane, A new synthetic method of this compound is introduced below., Safety of 7-(Bromomethyl)pentadecane
General procedure: The general procedure for the alkylation of fluorene (C-alkylation) is as follows. A two-neck flask with a three-way stopcock and a rubber septum was charged with fluorene (4mmol, 0.664 g) and dry THF (20 mL). KOtBu (12mmol, 1.346 g) was added to the flask at room temperature, then the mixture was heated at reflux for 20min. The flask was allowed to reach room temperature with stirring for 30min. 1-Bromododecane (8.8mmol, 2.20 g) was slowly added to the reaction mixture at 0 C, then again the flask was allowed to reach room temperature with stirring for overnight. 2.2.1 The First Posttreatment: After checking TLC and the 1HNMR spectrum, the reaction mixture refluxed for one hour. The reaction was quenched by the addition of sat. NH4Cl aqueous solution, extracted into n-hexane (50 3 mL), was hed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the reaction mixture(including the target dialkylated fluorene and olefin.). 2.2.2 The Second Posttreatment: 2-(a): To a mixtureof the crude mixture of the first posttreatment, 5wt% Pd/C(0.100 g) and acetic acid (AcOH, 4mmol) in THF (10 mL) were slowly added portionwise NaBH4 (4mmol, 0.151 g), andthe resulting mixture was stirred at room temperature for 12 hours. Thereafter, the mixture was filtered and the precipitate was washed with hexane and concentrated by rotary evaporatorfor NMR measurement. 2-(b): Since the alkylation was an almost quantitative reaction, the expected amount of olefin in the mixture was equalto the excess amount of starting alkyl halide (0.8mmol in the above case). It could be assumed that 0.8 mmol of olefin should be treated with the small excess of 9-BBN (1.2mmol, 1.5 eqvs olefin). A two neck flask with a three-way stopcock and a rubber septum was charged with the above reaction mixture and dry THF (20 mL). 0.5M 9-BBN in THF (1.2mmol, 2.4mL) was added to the flask at 0 C and then the flask was allowed to warm to room temperature and stirred for one hour. To quench the remaining 9-BBN in the reaction, aminoalcohol (2-dimethylaminoethanol, 0.5mmol, 0.045 g) was added to the flask and stirred for another hour. 39 The final reaction mixture was quenched by the addition of water (5 mL), extracted into EtOAc (50 3 mL), washed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the crude mixture. 2.2.3 The Third Posttreatment: The crude product was purified on short silica-gel [5 cm (diameter of column) 10 cm (length of deposition of silica-gel) was enough for this scale] with n-hexane as eluent to give the dialkylated fluorene.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Okamoto, Ken; Lu, Fengniu; Nakanishi, Takashi; Bulletin of the Chemical Society of Japan; vol. 91; 8; (2018); p. 1258 – 1263;,
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bromide – Wiktionary