반응 #340496

반응 방정식

water

(5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol

pyridine

thionyl chloride

→

1-(chloromethyl)-5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}benzene

수율 100.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate (3×20 mL)
2. 2
   추출The combined extract
3. 3
   세척was washed with water and brine (20 mL each)
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

To a solution of (5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (0.31 g, 1.1 mmol) and pyridine (0.15 mL 1.9 mmol) in tetrahydrofuran (10 mL) at 0° C. was added thionyl chloride (0.093 mL, 1.3 mmol) and the reaction mixture warmed to room temperature and stirred for one hour. Then it was poured into water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined extract was washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give 1-(chloromethyl)-5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}benzene (0.33 g, 1.1 mmol, 100% yield), 1H NMR (400 MHz, CDCl3): 6.76-6.26 (m, 2H), 4.69 (s, 2H), 4.22-4.13 (m, 4H), 3.86-3.78 (m, 4H), 3.46 (s, 6H).

출처