52997-43-0, 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. 52997-43-0, name is 7-(Bromomethyl)pentadecane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
The general procedure (Table 1, entry 5 and 6) for the synthesis of alkylation of aniline (N-alkylation) and phenol (O-alkylation) is as follows. A two neck flask with a three-way stopcock and a rubber septum was charged with aniline (4 mmol, 0.373 g), 1-bromododecane (15 mmol, 3.74 g), K2CO3 (8 mmol, 1.11 g) and dry DMF (3.0 mL). The flask was heated at 120 C overnight. The first posttreatment: After checking of TLC and 1H NMR spectrum (Figure S3(a)), KOtBu (12 mmol, 1.346 g) was added to the flask at room temperature, then the mixture was heated to reflux overnight. The reaction was quenched by the addition of sat. NH4Cl aqueous solution, extracted into CH2Cl2 (50 ¡Á 3 mL), washed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the reaction mixture (including target dialkylated aniline and corresponding olefin, Figure S3(b)).The second posttreatment: Since the N-alkylation was almost quantitative reaction, the expected amount of olefin in the mixture was equal to the excess amount of starting alkylhalide (7.0 mmol in the above case). It could be assumed that 7.0 mmol of olefin should be treated with the small excess of 9-BBN (10.5 mmol, 1.5 eq vs 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). 0.5 M 9-BBN in THF (10.5 mmol, 21 mL) was added to the flask at 0 C and then the flask allowed to warm to room temperature and stirred for one hour. To quench the remaining 9-BBN in the reaction, aminoalcohol (2-dimethylaminoethanol, 4.5 mmol, 0.405 g) was added to the flask and stirred for another one hour. The final reaction mixture was quenched by the addition of water (5 mL), extracted into EtOAc (50 ¡Á 3 mL), washed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the crude mixture (Figure S5(a)). The third post-treatment: The crude product was purified by short silica-gel column chromatography (5 cm (diameter of column) ¡Á 10 cm (length of deposition of silicag-gel was enough for this scale) with n-hexane as eluent to give the dialkylated aniline (Figure S5(b)).
The synthetic route of 7-(Bromomethyl)pentadecane has been constantly updated, and we look forward to future research findings.
Reference:
Article; Okamoto, Ken; Lu, Fengniu; Nakanishi, Takashi; Bulletin of the Chemical Society of Japan; vol. 91; 8; (2018); p. 1258 – 1263;,
Bromide – Wikipedia,
bromide – Wiktionary