Electric Literature of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.
A flask containing tetrahydrofuran (5.0 niL) was charged with sodium amide (109 mg, 2.65 mmol; Alfa Aesar), chilled to 0 0C, and treated with 2,1 l-dimethyl-5,6,7,8,9,10- hexahydro-7,10-epiminocyclohepta[delta]indole (300 mg, 1.326 mmol; Example IA), added in portions. After 5 minutes, the ice bath was removed and the mixture was heated to 60 0C for 15 minutes. The solution was cooled to room temperature and l-(2-bromoethoxy)-4- fluorobenzene (348 mg, 1.591 mmol; Aldrich) was added slowly. The reaction mixture was stirred overnight at room temperature, then diluted with water (5 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated in vacuo, and the resulting residue was purified by reverse- phase HPLC (Phenomenex Luna C8(2) 5 mum IOOA AXIA column, 30×75 mm, 10-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid, flow rate 50 mL/minute) to afford the title compound as the trifluoroacetic acid salt: 1H NMR (300 MHz, methanol-^) delta ppm 1.79 – 2.07 (m, 1 H), 2.12 – 2.30 (m, 1 H), 2.34 – 2.50 (m, 4 H), 2.50 – 2.66 (m, 1 H), 2.93 (s, 3 H), 3.02 – 3.20 (m, 1 H), 3.66 (d, J=17.1 Hz, 1 H), 4.13 – 4.37 (m, 3 H), 4.42 – 4.58 (m, 2 H), 4.93 – 5.12 (m, 1 H), 6.61 – 6.84 (m, 2 H), 6.81 – 7.01 (m, 2 H), 7.01 – 7.14 (m, 1 H), 7.31 (s, 1 H), 7.34 – 7.43 (m, 1 H); MS (ESI) m/z 365 (M+H)+.
The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ABBOTT LABORATORIES; SCHRIMPF, Michael R.; LEE, Chih-Hung; LI, Tao; GFESSER, Gregory A.; MORTELL, Kathleen H.; FAGHIH, Ramin; NERSESIAN, Diana L.; SIPPY, Kevin B.; BUNNELLE, William H.; SCANIO, Marc; SHI, Lei; GOPALAKRISHNAN, Murali; DONNELLY-ROBERTS, Diana; HU, Min; WO2010/36998; (2010); A2;,
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