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With bromine; sodium sulfite; In N-methyl-acetamide; water;
EXAMPLE 1 3-Chloro-5-octyl-2-(4-octyloxyphenyl)pyridine 10.5 ml (203.0 mmol) of bromine are added dropwise at 0° C. to 23.9 g (184.5 mmol) of 3-chloro-2-hydroxypyridine in 240 ml of dimethylformamide, and the mixture is stirred at room temperature for 2 hours. 200 ml of water are subsequently added, and 30 g of sodium sulfite in 100 ml of water are added dropwise. After 15 minutes, the mixture is extracted three times with 200 ml of dichloromethane in each case, the combined organic phases are dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness, giving 36.58 g of 5-bromo-3-chloro-2-hydroxypyridine. STR13 m.p.: 168° C. (decomp.)
36.0 g (172.7 mmol) of <strong>[58236-70-7]5-bromo-3-chloro-2-hydroxypyridine</strong> are stirred at 160° C. for 6 hours in 320 ml of phosphorus tribromide. The reaction mixture is cooled to room temperature and poured carefully into ice water. After 2 hours, the mixture is extracted three times with 500 ml of dichloromethane in each case. The combined organic phases are washed with sodium bicarbonate solution until neutral, dried over Na2 SO4 and filtered, and the filtrate is evaporated to dryness. Chromatographic purification (silica gel/dichloromethane) gives 20.53 g of 3-chloro-2,5-dibromopyridine. STR14 m.p.: 40°-41° C.
5-bromo-3-chloro-2-((tetrahydro-2H-pyran-4-yl)oxy)pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 18.0h;
Step2: 5-Bromo-3-chloro-2-((tetrahydro-2H-pyran-4-yl)oxy)pyridine[254][255]Potassium carbonate (2.0 eq.) was added to a solution of tetrahydro-2H-pyran-4-yl methanesulfonate (1.2 eq.) and 5-bromo-3-chloropyridine-1-ol (1.0 eq.) in N,N-dimethylformamide (0.2 M). The reaction mixture was stirred at 100 for 18 h. The reaction mixture was allowed to reach room temperature, diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. The resultant residue was purified by flash column chromatography on silica gel to afford 5-bromo-3-chloro-2-((tetrahydro-2H-pyran-4-yl) oxy) pyridine.
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