Acetic Acid → 3-Bromo-2-fluoro-6-methoxybenzaldehyde

Temperatur

-78 °C

To a solution of 4-bromo-3-fluoroanisole (10 g, 48.7 mmol, Matrix) in tetrahydrofuran (100 mL) at −78° C. was added lithium diisopropyl amine (32.5 mL, 1.8 M in THF, 58.4 mmol) dropwise during a period of 15 min. The mixture was stirred at −78° C. for another 20 mins. Then N,N-dimethyl-formamide (4.53 mL, 58.4 mmol) was added in one portion. The mixture was stirred at −78° C. for 10 min, then quenched with acetic acid (12 g, 194 mmol) and followed by the addition of water (61 mL). The mixture was partitioned between ethyl acetate and water. The organic layer was separated, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:4) to give 3-bromo-2-fluoro-6-methoxy-benzaldehyde as a yellow solid (Yield: 10 g, 89%)

1. stirringThe mixture was stirred at −78° C. for 10 min
2. customThe mixture was partitioned between ethyl acetate and water
3. customThe organic layer was separated
4. concentrationconcentrated
5. customThe residue was purified by chromatography (EtOAc:hexanes=1:4)

ORD-Eintrag

ord-f6d740b1e3b34751afb97d2e9fdbdb75

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08134001B2