N-bromobutanimide → 2-Amino-5-bromo-4-chloropyridine

To a stirred solution of 4-chloropyridin-2-amine (8 g, 62.2 mmol) in acetonitrile (600 mL) at rt was added N-bromosuccinimide (11.08 g, 62.2 mmol) in portions and the reaction was stirred for 14 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (100 mL), brine (100 mL) and dried over sodium sulfate. The organics were concentrated under reduced pressure to afford 5-bromo-4-chloropyridin-2-amine as yellow solid (13 g, 99%) that was used as is without further purification. LC/MS (ESI) m/e 207.0 [(M+H)+, calcd for C5H5BrClN2 206.9]; LC/MS retention time (method B): tR=0.8 min.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionThe residue was diluted with water (50 mL)
3. extractionextracted with EtOAc (3×50 mL)
4. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
5. dry with materialdried over sodium sulfate
6. concentrationThe organics were concentrated under reduced pressure

ORD record

ord-6312c11ef0ed4a2abd0d7d6af9ee991e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2