Extracurricular laboratory: Synthetic route of 2-Bromo-4-fluoroaniline

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

1003-98-1, name is 2-Bromo-4-fluoroaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 2-Bromo-4-fluoroaniline

Example 25Synthesis of 2-Bromo-4-Fluoro-5-Nitroaniline2-Bromo-4-fluoroaniline (47.5 g, 250 mmol) was added to a solution of concentrated H2SO4 (300 mL) keeping the internal temperature below 30 C. The mixture was aged for ca. 30-60 minutes then cooled to -20 C. 90% HNO3 (35 g) was added dropwise over ca. 60 minutes keeping the internal temperature between -15 to -20 C. TLC indicated a slight amount of starting material, so a further aliquot of 90% HNO3 (3 g) was added over 5 minutes at -15 to -20 C. The cold mixture was then poured on to ice H2O (ca. 1 L ice+500 mL H2O) and EtOAc (1 L). The aqueous and organic layers were partitioned and the organic layer was washed with saturated NaHCO3 (2×500 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a dark solid (35 g, 60%).1H NMR (DMSO-d6, 300 MHz): delta 8.27 (br. S, 2H), 7.70 (d 1H), 7.47 (d, 1H); m/z=275.9 (M+MeCN+H)+ for 79Br.

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Singh, Rajinder; Tso, Kin; Zhang, Jing; Duncton, Matthew; Alvarez, Salvador; Kolluri, Rao; Ramphal, John; Holland, Sacha; US2011/130415; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary