Dimethylformamide → 2-Bromo-3,6-difluorobenzaldehyde

Temperature

-78 °C

To solution of diisopropylamine (13.29 mL, 93 mmol) in THF (300 mL) at −78° C., was added n-butyllithium (34.2 mL of 2.5M in hexanes, 85 mmol), dropwise over 10 mins. The mixture was stirred at −78° C. for 15 mins and then 2-bromo-1,4-difluorobenzene (15 g, 78 mmol) in THF (100 mL) was added dropwise over 15 mins maintaining the temperature below −65° C. After stirring for 1 hr at −78° C., N,N-dimethylformamide (6.62 mL, 85 mmol) was added via syringe. The mixture was stirred at −78° C. for 30 mins and then quenched with sat. NH4Cl solution and the mixture was allowed to reach room temperature. The product was extracted into ether and the extracts were dried (Na2SO4) and evaporated. Chromatography (silica, 0-100% dichloromethane in hexane) gave the title compound (D14) as a yellow solid (12.73 g)

1. temperaturemaintaining the temperature below −65° C
2. stirringAfter stirring for 1 hr at −78° C.
3. stirringThe mixture was stirred at −78° C. for 30 mins
4. customquenched with sat. NH4Cl solution
5. customto reach room temperature
6. extractionThe product was extracted into ether
7. dry with materialthe extracts were dried (Na2SO4)
8. customevaporated

ORD record

ord-41af9c58072c451580d0cd65825695ec

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960563B2