3-Bromopyridine → 3-(Trimethylstannyl)pyridine

Temperature

-78 °C

To a stirred solution of 3-bromopyridine (1.58 g, 10 mmol) in anhydrous ethyl ether (100 mL) at −78° C. was added n-butyl lithium (1.6M in hexane, 7.5 mL) via a syringe, and the resulting solution was stirred at −78° C. for 10 minutes. Trimethyltin chloride (2.39 g, 12 mmol) was then added, and the mixture was stirred at −78° C. for 20 minutes, and then warmed to room temperature over 1 hour. The reaction mixture was diluted with hexanes (30 mL) and washed with water. The organic phase was dried and concentrated to give the crude product which was purified by vacuum distillation (125° C. at 15-20 mmHg) to give 3-trimethylstannyl pyridine (1.93 g, 80% yield).

1. stirringthe mixture was stirred at −78° C. for 20 minutes
2. temperaturewarmed to room temperature over 1 hour
3. washwashed with water
4. customThe organic phase was dried
5. concentrationconcentrated
6. customto give the crude product which
7. distillationwas purified by vacuum distillation (125° C. at 15-20 mmHg)

ORD record

ord-1b67cfb617644c1b8fcf3f6b0d9397ab

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07288567B2