3-BROMO-2,6-DIFLUOROBENZALDEHYDE synthesis

Yield:-

Reaction Conditions:

with lithium diisopropyl amide in tetrahydrofuran;N-methyl-acetamide;water

Steps:

106.a a)
a) 3-Bromo-2,6-difluorobenzaldehyde To a solution of 1-bromo-2,4-difluorobenzene (1.36 g, 7 mmol) in dry THF (20 mL) at -78° C. under nitrogen was added lithium diisopropylamide (2M in THF) (3.5 mL, 7 mmol) and stirred for 1h. Dimethylformamide (0.545 mL, 7 mmol) was added and stirred at -78° C. for 30 min. The reaction was quenched with acetic acid and extracted from water into dichloromethane. The organic extracts were washed with 1M hydrochloric acid, aqueous sodium hydrogen carbonate and brine, dried (MgSO₄), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluding with ethyl acetate/hexane (3:17), to yield the title compound as a yellow solid.

References:

Agejas-Chicharro, Javier;Belen Bueno Melendo, Ana;Camp, Nicholas Paul;Gilmore, Jeremy;Jimenez-Aguado, Alma Maria;Lamas-Peteira, Carlos;Marcos-Llorente, Alicia;Mazanetz, Michael Philip;Montero Salgado, Carlos;Timms, Graham Henry;Williams, Andrew Caerwyn US2004/122001, 2004, A1