反応 #308952

反応方程式

ethylbromodifluoroacetate

NH4Cl

5-bromo-2-fluorobenzaldehyde

Indium

→

title compound

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

溶媒

DMF

DMF

反応条件

後処理

1. 1
   workup.ADDITIONwas added to the resultant
2. 2
   その他reaction mixture and temperature of the reaction mixture
3. 3
   その他Reaction mixture
4. 4
   抽出the crude product was extracted with ethyl acetate (500 mL)
5. 5
   洗浄by washing with water, brine
6. 6
   乾燥the organic layer was dried over anhydrous Na2SO4
7. 7
   濃縮The organic layer was concentrated
8. 8
   その他the crude product was purified by column chromatography on silica gel using 4% Ethyl acetate in Hexane

実験手順

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%).

出典