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Pyridine (250 mL) was added to a 2 liter flask equipped with a mechanical stirrer, a reflux condenser and a nitrogen inlet. The flask was cooled in an ice bath and 2,4,6-trimethylphenol (42.5 g, 0.312 mol) and potassium t-butoxide (35.1 g, 0.313 mol) were added. The flask was warmed to room temperature and 2,4-dichloro-3,6-dimethylpyridine (50.0 g, 0.284 mol) and copper (I) iodide (13.5 g, 0.071 mol) were added. The reaction mixture was heated under reflux for two hours and then cooled to 0° C. The reaction mixture was diluted with hexanes (500 mL) and mixed with saturated ammonium chloride (NH4Cl, 1000 mL). After warming to room temperature, the mixture was stirred overnight. The layers were separated and the organic layer was washed with 3×125 mL of 1N hydrochloric acid (HCl) and 1×250 mL of water. After drying over sodium sulfate (Na2SO4), the solids were removed by filtration and washed with hexanes. The filtrate was concentrated under vacuum to afford a brown oil. The residue was mixed with methanol (250 mL) and was stirred overnight. The resulting slurry was filtered under vacuum. The off-white solids were washed with methanol then dried to afford 31.6 g (40.4%) of the title compound of Preparation F. 1HNMR (CDCl3): δ 6.88 (s, 2H), 6.78 (s, 1H), 2.40 (s, 3H), 2.30 (s, 3H), 2.20 (s, 3H), 2.04 (s, 6H).

1. customequipped with a mechanical stirrer, a reflux condenser and a nitrogen inlet
2. temperatureThe flask was cooled in an ice bath
3. temperatureThe reaction mixture was heated
4. temperatureunder reflux for two hours
5. temperaturecooled to 0° C
6. temperatureAfter warming to room temperature
7. customThe layers were separated
8. washthe organic layer was washed with 3×125 mL of 1N hydrochloric acid (HCl) and 1×250 mL of water
9. dry with materialAfter drying over sodium sulfate (Na2SO4)
10. customthe solids were removed by filtration
11. washwashed with hexanes
12. concentrationThe filtrate was concentrated under vacuum
13. customto afford a brown oil
14. stirringwas stirred overnight
15. filtrationThe resulting slurry was filtered under vacuum
16. washThe off-white solids were washed with methanol
17. customthen dried
18. customto afford