Dichloromethane → HCID 178419376, compound

Participants

Reaction Conditions

Reaction Steps

See Scheme 3. Toluene (15 mL) was added to 2,6-dibromopyridine (0.341 g, 1.44 mmol, purchased from Sigma-Aldrich) and ferrocenylboronic acid (0.321 g, 1.40 mmol, purchased from Sigma-Aldrich) to form an orange suspension. A suspension of (dppf)PdCl2.CH2Cl2 (0.047 g, 0.058 mmol, purchased from Strem) (dppf=1,1′-bis(diphenylphosphino)ferrocene) in toluene (5 mL) was then added followed by a 1 M solution of Na2CO3 (10 mL, 10 mmol) in 4:1 water:methanol. The biphasic mixture was heated to 60° C. for 23 hours. At this time 1H NMR spectroscopic analysis indicated approximately 45% conversion to the desired product. The organic layer was separated, washed with a little water and then brine. The organics were then dried over MgSO4 and filtered. Removal of the volatiles afforded an orange residue. The remaining 2,6-dibromopyridine was removed by sublimation at 45° C./ca. 100 mTorr over 2 hours. The crude was purified on an Al2O3 column using 4% ethyl acetate in hexane as the elutant. The product was still contaminated with some 2,6-diferrocenylpyridine. Pure 2-bromo-6-ferrocenylpyridine was isolated by crystallization from hexamethyldisiloxane. Yield: 0.058 g (12%). 1H NMR(C6D6): δ 6.87 (1H, d), 6.79 (1H, d), 6.64 (1H, t), 4.83 (2H, m), 4.11 (2H, m), 3.83 (5H, s).

Provenance & Evidence