تفاعل #2336546

معادلة التفاعل

3-bromo-6-chloro-2-fluorophenol

sodium hydride

methanesulfonic acid 2,2 difluoroethyl ester

→

1-bromo-4-chloro-3-(2,2-difluoroethoxy)-2-fluorobenzene

المردود 45.6%

المذيبات

water

DMF

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl ether
2. 2
   تجفيفThe combined organic phases were dried (sodium sulfate)
3. 3
   تركيزconcentrated
4. 4
   أخرىThe residual oil was purified by chromatography (in hexanes)

الإجراء التجريبي

A solution of 3-bromo-6-chloro-2-fluorophenol (15.4 g, 0.068 mol) in DMF (25 mL) was slowly added to a suspension of sodium hydride (60% dispersion in mineral oil) (4.0 g, 0.10 mol) in DMF (100 mL) and the mixture was stirred 1 hour. A solution of methanesulfonic acid 2,2 difluoroethyl ester (17.5 g, 0.109 mol) in DMF (10 mL) was slowly added. The resulting solution was heated to 70° C. for 18 hours. The solution was diluted with water (200 mL) and extracted with ethyl ether. The combined organic phases were dried (sodium sulfate) and concentrated. The residual oil was purified by chromatography (in hexanes) to give 1-bromo-4-chloro-3-(2,2-difluoroethoxy)-2-fluorobenzene (9.0 g, 0.031 mol): 1H NMR (CDCl3): δ 7.3 (m, 1H), 7.10 (dd, 1H), 6.15 (dt, 1H), 4.35 (m, 2H).

المصدر