Electric Literature of 1073-06-9,Some common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, molecular formula is C6H4BrF, 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.
Step 1: 2-Bromo-6-fluorobenzaldehydeTo a stirred solution of diisopropylamine (1.4 mL, 0.00571 mol) in dry tetrahydrofuran (7.2 mL) was added dropwise n-butyllithium (1.6M in hexane) (3.56 mL, 0.00571 mol) at 0C and stirring was continued for 15 min at 0C. The reaction mixture was cooled to -78C and l-bromo-3-fluorobenzene (1 g, 0.00571 mol) was added over 10 min. After stirring for 1 h at -78C, anhydrous N,N-dimethylformamide (7.2 mL) was added dropwise over 5 min and the resulting mixture was stirred for another 20 min at -78C. The reaction was quenched with addition of acetic acid (0.6 mL) followed by water (15 mL) and the mixture was warmed to room temperature. The mixture was extracted with ethyl acetate (2×20 mL) and the combined organic layers were washed with water (2×10 mL) followed by brine solution and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum to afford the title compound as a pale yellow solid (850 mg, 73%). H NMR (400 MHz, DMSO-d6) : delta 10.21 (s, 1H), 7.66-7.61 (m, 2H), 7.45-7.42 (m, 1H). ESI-MS: Calculated mass: 201.94; Observed mass: 202.0 [M]+.
The synthetic route of 1073-06-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; SMITH, Roger, A.; REDDY, Sanjeeva; JOHN, Tyler, M.; NYAVANANDI, Vijay, Kumar; SUBRAMANYA, Hosahalli; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; NADIPALLI, Prabhakara, Rao; SENGUPTA, Saumitra; WO2014/169167; (2014); A1;,
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