Reference of 179898-34-1, A common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.
Example 18 1,1-Dimethylethyl [(3-bromo-5-fluorophenyl)methyl]carbamate NaBH4 (1.99 g, 52.5 mmol) was cautiously added to a solution of NiCl2 (1.36 g, 10.5 mmol), Boc2O (4.58 g, 21.0 mmol) and 3-bromo-5-fluorobenzonitrile (2.10 g, 10.5 mmol) in absolute ethanol (30 mL) at 0 C. (vigorous reaction with the formation of a black precipitate). Once the reaction had subsided the mixture was left to stir at room temperature for 30 min. Ethanol was removed under reduced pressure and the precipitate was dissolved in EtOAc, filtered and repeatedly washed with EtOAc. The combined organic phase was washed with saturated NaHCO3, and dried over Na2SO4. After removing the solvent, the product was purified by flash column chromatography to yield 1,1-dimethylethyl [(3-bromo-5-fluorophenyl)methyl]carbamate (2.20 g, 69%). 1H NMR (400 MHz, CDCl3): delta 1.46 (S, 9H), 4.28-4.32 (m, 2H), 4.87 (br, 1H), 6.93-7.29 (m, 3H); 13C NMR (100 MHz, CDCl3): delta 20.3, 43.6, 44.1, 79.7, 80.0, 113.0, 114.0, 117.7, 122.5, 126.0, 123.0, 141.7, 155.9, 161.5, 164.0.
The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Glaxo Group Limited; US2009/197871; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts