Chlorotrimethylsilane → 2,6-Dichloro-4-trifluoromethyl-3-trimethylsilanylpyridine

Participants

Reaction Conditions

Reaction Steps

A dry 100 mL 3 neck rb flask was charged with diisopropylamine (2.15 mL, 15.3 mmol) and 40 mL of anhydrous THF. Reaction mixture was cooled at −20° C. under N2. A 2.5 M solution of n-BuLi in Hexane (5.90 mL, 14.8 mmol) was added dropwise via a syringe. The resulting reaction mixture was then cooled at −78° C. A solution of 2,6-dichloro-4-trifluoromethylpyridine (3.0 g, 14 mmol) in 5 mL of anhydrous THF was added slowly via an addition funnel to give a pale yellow solution. Reaction mixture stirred at −78° C. for 2 h. After which time, a solution of TMSCl (2.0 mL, 15.8 mmol) in 5 mL of THF was added dropwise via an addition funnel. The resulting reaction mixture was allowed to slowly warm up to room temperature and stirred over night. Reaction mixture was added to 150 mL of Et2O, washed with dilute HCl, then washed with aq. NaHCO3, dried over MgSO4, filtered and concentrated to give 3.80 g (95%) of 2,6-dichloro-4-trifluoromethyl-3-trimethylsilanylpyridine (Compound 8) as a brown oil:

Provenance & Evidence