Reference of 6091-64-1, These common heterocyclic compound, 6091-64-1, name is Ethyl 2-bromobenzoate, 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.
To a tube was added Hphosphinate 3a (173 mg, 1 mmol, 1 equiv), Pd(OAc)2 (4.5 mg, 0.02 mmol, 2 mol %), xantphos (12.7 mg, 0.022 mmol, 2.2 mol %), toluene and 1,2-dimethoxyethane (4.5 ml : 0.5 ml), i-Pr2NEt (0.23 ml, 1.3 mmol, 1.3 equiv) and ethyl-2-bromobenzoate (0.24 mL, 1.5 mmol, 1.5 equiv). The homogeneous mixture was stirred under a flow of N2 for 10 minutes and then heated at 115C for 24 hrs. The solvent was then evaporated and the resulting residue partitioned between EtOAc (10 ml) and NaHCO3 (5 ml). The aqueous layer was extracted with EtOAc (3x). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The resulting oil was then purified by chromatography (silica gel, hexane/ EtOAc, 5:5) to give a yellow oil. Yield: 83% (232 mg); 1H NMR (CDCl3, 300 MHz) delta 8.04-8.11 (m, 1H), 7-77-7.81 (m, 1H), 7.59-7.64 (m, 2H), 4.41 (q, J = 7.0 Hz, 2H), 3.75-4.07 (dm, 2H), 1.90 (d, J = 15.2 Hz, 3H), 1.60-1.67 (m, 2H), 1.35-1.47 (m, 5H), 0.92 (t, J = 7.3 Hz, 3H) ppm; 13C NMR (CDCl3, 75.45 MHz) delta 168.1 (d, JPCCC = 3.4 Hz), 135.9 (d, JPCCC = 7.8 Hz), 133.9 (d, JPCCC = 8.1 Hz), 132.0 (d, JPCCCC = 2.3 Hz), 131.6 (d, JPC = 120.6 Hz), 131.0 (d, JPCC = 11.5 Hz), 129.7 (d, JPCC = 9.8 Hz), 64.5 (d, JPOC = 6.3 Hz), 61.9, 32.6 (d, JPOCC = 6.6 Hz), 18.9, 17.3 (d, JPC = 103.9 Hz), 14.2, 13.7 ppm; 31P NMR (CDCl3, 121.47 MHz) delta 43.07 ppm; HRMS (EI+) calcd for C14H21O4P 284.1177, found 284.1179.
Statistics shows that Ethyl 2-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 6091-64-1.
Reference:
Article; Gavara, Laurent; Petit, Christelle; Montchamp, Jean-Luc; Tetrahedron Letters; vol. 53; 37; (2012); p. 5000 – 5003;,
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