These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, 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. category: ethers-buliding-blocks
Intermediate 1: 2-propyl-4-(trifluoromethoxy)aniline A solution of 2-bromo-4-(trifluoromethoxy)aniline (256 mg, 1.00 mmol), [(E)-prop-1-enyl]boronic acid (172 mg, 2.00 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (29.0 mg, 0.0400 mmol), and K2CO3(aq) (1 M, 2 equiv) in MeOH (0.5 mL)/toluene (0.5 mL) was stirred at 125 C. for 4 h. The organic layer was separated, concentrated to dryness, and purified by FCC (SiO2) to give (E)-2-(prop-1-en-1-yl)-4-(trifluoromethoxy)aniline. (E)-2-(Prop-1-en-1-yl)-4-(trifluoromethoxy)aniline and Pd/C (10% on carbon, 30 mg) in MeOH (10 mL) was stirred under H2 (1 atm) for 3 h. After filtration on diatomaceous earth such as Celite, the filtrate was collected and concentrated to dryness to give 2-propyl-4-(trifluoromethoxy)aniline. MS (ESI): mass calcd. for C10H12F3NO, 219.1; m/z found, 220.1 [M+H]+.
The synthetic route of 2-Bromo-4-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Janssen Pharmaceutica NV; Bacani, Genesis M.; Chai, Wenying; Edwards, James P.; Smith, Russell C.; Tichenor, Mark S.; Venable, Jennifer D.; Wei, Jianmei; (64 pag.)US2018/289706; (2018); A1;,
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