Ammonium Chloride → HCID 55071267, compound

Temperature

30 °C

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%).

1. additionwas added to the resultant
2. customreaction mixture and temperature of the reaction mixture
3. customReaction mixture
4. extractionthe crude product was extracted with ethyl acetate (500 mL)
5. washby washing with water, brine
6. dry with materialthe organic layer was dried over anhydrous Na2SO4
7. concentrationThe organic layer was concentrated
8. customthe crude product was purified by column chromatography on silica gel using 4% Ethyl acetate in Hexane

ORD record

ord-618601587a834845920b5ae396cbdde0

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207164B2