Application of 55666-42-7, A common heterocyclic compound, 55666-42-7, name is tert-Butyl 2-bromobenzoate, molecular formula is C11H13BrO2, 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-Butyl 2-bromobenzoate (800 mg, 3.11 mmol) and anhydrous THF (5 mL) were added to a dried flask under an argon atmosphere. The mixture was cooled to -78 C., and then 1 M sec-butyllithium (2.0 mmol) was added thereto, and the mixture was stirred for 20 minutes. 3,6-DiOTBDMS-Si-xanthone (40.0 mg, 0.0802 mmol) dissolved in anhydrous THF (5 mL) was slowly added to the mixture at the same temperature, and the mixture was brought to room temperature. The mixture was stirred at room temperature for 30 minutes, and then 2 N hydrochloric acid (10 mL) was added thereto, and the mixture was stirred for 20 minutes. The mixture was extracted with dichloromethane, and the organic layer was washed with brine, and dried over sodium sulfate. The solvent was removed, then trifluoroacetic acid (TFA, 3 mL) was added to the residue, and the mixture was stirred at room temperature for 1 hour. The solvent was removed, and then the residue was purified by HPLC to obtain 2-COOH TM (13.6 mg, 0.0358 mmol, yield 45%). (0205) 1H-NMR (300 MHz, CD3COCD3): delta 0.56 (s, 3H), 0.64 (s, 3H), 6.76 (dd, 2H J=2.9, 8.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 7.23 (d, 2H J=2.9 Hz), 7.38 (d, 1H, J=7.3 Hz), 7.67 (td, 111, J=1.5, 7.3 Hz), 7.80 (td, 1H, J=1.5, 7.3 Hz), 7.94 (dd, 1H, J=1.5, 7.3 Hz) (0206) 13C-NMR (100 MHz, CD3COCD3): delta -1.4, 0.2, 91.1, 117.6, 121.1, 125.5, 126.3, 127.0, 129.3, 130.1, 135.1, 136.7, 138.2, 155.3, 157.7, 170.4 (0207) HRMS (ESI+): m/z Found 375.1018. calculated 375.1053 for [M+H]+ (-3.5 mmu)
The synthetic route of 55666-42-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; THE UNIVERSITY OF TOKYO; Nagano, Tetsuo; Hanaoka, Kenjiro; Koide, Yuichiro; Egawa, Takahiro; US9170266; (2015); B2;,
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