반응 #340485

반응 방정식

(8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol

triethylamine

thionyl chloride

→

7-(chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine

수율 99.8%

용매

dichloromethane

Dichloromethane

반응 조건

후처리

1. 1
   기타at 0° C
2. 2
   workup.WAITat rt for 3 h
3. 3
   세척the solution was washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL)
4. 4
   건조brine (40 mL) and dried over sodium sulfate
5. 5
   여과Filtration and concentration

실험 절차

To a solution of (8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol (0.84 g, 4.55 mmol) and triethylamine (960 μl, 4.84 mmol) in dichloromethane (20 mL) was slowly added thionyl chloride (400 μl, 5.47 mmol) at 0° C. The solution was stirred at 0° C. for 15 min then at rt for 3 h. Dichloromethane (80 mL) was added and the solution was washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL) then brine (40 mL) and dried over sodium sulfate. Filtration and concentration gave 7-(chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine (0.92 g, quantitative yield) as a brown oil. The chloride was used in the next step without further purification.

출처