Sodium Iodide → 5-Bromo-2-iodo-4-(trifluoromethyl)pyridine

Temperature

40 °C

Prepared using General Procedure 17: To a stirred a solution of 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (150 mg, 0.576 mmol) in acetonitrile (2 mL) was added sodium iodide (518 mg, 3.45 mmol). The reaction mixture was heated to 40° C. and acetyl chloride (26.0 mg, 0.345 mmol) was added. The reaction mixture was stirred at 40° C. for 90 min. Once cooled, the reaction was quenched with NaHCO3 (5 mL) and extracted with EA (3×5 mL). The combined organics were washed with brine (10 mL), dried over MgSO4 and concentrated to give 80.0 mg (40%) of 5-bromo-2-iodo-4-(trifluoromethyl)pyridine as a white crystalline solid which was used in the subsequent step without purification. LCMS-ESI (m/z) calculated for C6H2BrF3IN, 351.9; found 352.5 [M+H]+, tR=3.91 min. (Method 1).

1. customPrepared
2. temperatureOnce cooled
3. customthe reaction was quenched with NaHCO3 (5 mL)
4. extractionextracted with EA (3×5 mL)
5. washThe combined organics were washed with brine (10 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-464989555c544e2e88602811bc6bd018

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778923B2