반응 #308952

반응 방정식

ethylbromodifluoroacetate

NH4Cl

5-bromo-2-fluorobenzaldehyde

Indium

→

title compound

Ethyl 3-(5-bromo-2-fluorophenyl)-2,2-difluoro-3-hydroxypropanoate

용매

DMF

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the resultant
2. 2
   기타reaction mixture and temperature of the reaction mixture
3. 3
   기타Reaction mixture
4. 4
   추출the crude product was extracted with ethyl acetate (500 mL)
5. 5
   세척by washing with water, brine
6. 6
   건조the organic layer was dried over anhydrous Na2SO4
7. 7
   농축The organic layer was concentrated
8. 8
   기타the crude product was purified by column chromatography on silica gel using 4% Ethyl acetate in Hexane

실험 절차

To an ice cooled solution of 5-bromo-2-fluorobenzaldehyde (10.0 g, 49.2 mmol) in dry DMF (14 mL), Indium powder (8.48 g, 73.7 mmol) was added and stirred for 15 min. ethylbromodifluoroacetate (9.48 ml [14.98 g], 73.7 mmol) in dry DMF (10 mL) was added to the resultant reaction mixture and temperature of the reaction mixture was allowed to warm to rt (30° C.). Stirring continued for 24 h. TLC analysis of the reaction mixture indicated the product formation. Reaction mixture was treated with aqueous saturated NH4Cl solution and the crude product was extracted with ethyl acetate (500 mL) by washing with water, brine and the organic layer was dried over anhydrous Na2SO4. The organic layer was concentrated and the crude product was purified by column chromatography on silica gel using 4% Ethyl acetate in Hexane to obtain title compound as a colorless thick liquid. Yield=12.0 g (75%).

출처