Electric Literature of 53087-13-1, 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
General procedure: To a 30 mL flamed-dried flask equipped with stir bar and a nitrogen-filled balloon were added 2,2,6,6-tetramethylpiperidine (1.2 equiv) and THF (12 mL). After cooled to 0 C with an ice waterbath, n-BuLi (2.5 M in hexane, 1.2 equiv) was added dropwise and the reaction was stirred at 0 C for 0.5 h. To a 100 mL flame-dried flask equipped with a stir bar and a nitrogen-filled balloon were added THF (30 mL), benzyne precursor (1 equiv), and corresponding ketene silyl acetals9 (1.5 equiv) and was cooled to 78 C with an acetone-dry ice bath before in situ generated lithium tetramethylpiperidine was added dropwise. The reaction was monitored and aqueous NH4Cl was added upon disappearance of the benzyne precursor. After warming to rt, the reaction mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and concentrated under reduced pressure. Acetonitrile (30 mL) was added to the concentrated reaction system and cooled to 0 C with an ice-water bath followed by slow addition of hydrofluoric acid (27.6 M, 10 equiv). Upon completion, the reaction was heated to 40 C overnight before water (100 mL) was added. The mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and dried with Na2SO4. The combined organic extract was concentrated under reduced pressure and purified by column chromatography on silica gel to afford the following compounds. 4.6.2. 8-Ethyl-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one (10). Compound 10 was obtained as colorless oil (876 mg) from 6a and tert-butyl((1-methoxybut-1-en-1-yl)oxy)dimethylsilane in 62% yield, Rf=0.8 (Hexane/EtOAc=5:1); 1H NMR (400 MHz, CDCl3) delta 7.40 (dd, J8.4, 7.1 Hz, 1H), 6.99 (d, J7.1 Hz, 1H), 6.78 (d, J8.4 Hz,1H), 4.13-4.06 (m, 4H), 1.98-1.72 (m, 2H), 1.04 (t, J7.5 Hz, 3H). 13C NMR (101 MHz, CDCl3) delta 188.9 (s), 156.0 (s), 153.5 (s), 137.5 (s), 131.1(s), 116.0 (s), 114.6 (s), 65.0 (s), 59.7 (s), 23.3 (s), 11.5 (s). IR: gamma 2963, 2934, 2876, 2359, 2340, 1766, 1602, 1574, 1482, 1455, 1435, 1277, 1157, 1123, 1020, 941, 799 cm-1. HRMS calcd for C16H14NaO2[MNa]: 261.0886, found: 261.0879.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Chen; Savage, Nikolas A.; Dong, Guangbin; Tetrahedron; vol. 70; 27-28; (2014); p. 4135 – 4146;,
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