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compound 18b

Methyl 4-(2-phenyl-1,3-dithiolan-2-yl)benzoate

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

HF-pyridine

→

compound 18c

Methyl 4-(difluoro(phenyl)methyl)benzoate

용매

CH2Cl2

CH2Cl2

polyethylene

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후처리

1. 1
   추출The solution was extracted with CH2Cl2
2. 2
   건조the combined organics were dried over anhydrous Na2SO4
3. 3
   농축concentrated
4. 4
   기타A crude product was purified by flash column chromatography (silica gel, 5% EtOAc/hexanes)

실험 절차

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) (381 mg, 1.07 mmol) and HF-pyridine reagent (1.5 mL, HF:Pyridine=70:30 wt %) were dissolved in CH2Cl2 (4 mL) in a polyethylene bottle and cooled to 0° C. A solution of compound 18b (162 mg, 0.512 mmol) in CH2Cl2 (2 mL) was slowly added and the mixture was stirred for 45 min at room temperature. The solution was extracted with CH2Cl2, and the combined organics were dried over anhydrous Na2SO4 and concentrated. A crude product was purified by flash column chromatography (silica gel, 5% EtOAc/hexanes) to afford compound 18c as a clear oil.

출처