Reference of 588-63-6, A common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
tert-BuLi (12 mL of a 1.7 M solution, 20 mmol) was added dropwise to a solution of 4-bromo-N,N-dimethylaniline (2.00 g, 10 mmol) in THF (40 mL) at 78° C. The resulting solution was stirred at 78° C. for 1 hour and was then warmed to ambient temperature. Tellurium powder (1.28 g, 10 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 1 hour. 1-Bromo-3-phenoxypropane (2.04 g, 9.5 mmol) in 5 mL of THF was added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was filtered through Celite and the filter cake was washed with CH2Cl2 (50 mL). The filtrate was concentrated and the residue was partitioned between H2O (100 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted with additional CH2Cl2 (3*25 mL). The combined organic extracts were dried over MgSO4 and concentrated. The crude product was then purified by column chromatography on silica gel eluted with 60percent CH2Cl2/hexanes to give 1.9 g (52percent) of 23b as an orange oil: 1H NMR (400 MHz, CDCl3) 7.63 (d, 2H, J=8.8 Hz), 7.24 (t, 2H, J=7.8), 6.91 (t, 1H, J=7.2), 6.84 (d, 2H, J=8.0 Hz), 6.54 (d, 2H, J=8.8 Hz), 3.97 (t, 2H, J=6.0 Hz), 2.94 (s, 6H), 2.90 (t, 2H, J=7.4 Hz), 2.20 (quint, 2H, J=6.8 Hz); 13C NMR (75 MHz, CDCl3) delta 158.9, 150.3, 141.2, 129.4, 120.6, 114.5, 113.4, 94.7, 68.7, 40.2, 31.2, 4.3; High Resolution MS (EI) m/z 385.0694 (Calcd for C17H21NO130 Te: 385.0681). Anal. Calcd for C17H21NOTe: C, 53.32; H, 5.53; N, 3.66. Found: C, 53.26; H, 5.61; N, 3.32.
The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; The Research Foundation of State University of New York; US2008/26027; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem