3-Bromo-4-fluorobenzaldehyde → 3-Cyclopropyl-4-fluorobenzaldehyde

Temperatur

50 °C

A flask was charged with cyclopropyl magnesium bromide (29.6 ml, 14.8 mmol) and placed under nitrogen. Zinc chloride (14.8 ml, 14.8 mmol) was added and the reaction was stirred for 20 minutes. 3-Bromo-4-fluorobenzaldehyde (1.0 g, 4.93 mmol) and bis(tri-t-butylphosphine)palladium (0) (0.126 g, 0.246 mmol) were diluted in 600 μL of THF and added to the reaction mixture. After stirring for 4 hours, the reaction was heated to 50° C. and stirred overnight. The reaction was cooled and quenched with saturated NH4Cl and extracted with DCM. The organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 40M cartridge eluting with hexanes:ethyl acetate (4:1) to yield 3-cyclopropyl-4-fluorobenzaldehyde (400 mg, 49.5% yield)

1. additionadded to the reaction mixture
2. stirringAfter stirring for 4 hours
3. stirringstirred overnight
4. temperatureThe reaction was cooled
5. customquenched with saturated NH4Cl
6. extractionextracted with DCM
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe material was purified
11. washeluting with hexanes:ethyl acetate (4:1)

ORD-Eintrag

ord-ca4eb11cdd5242c3aeed938e9954eb2c

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08183289B2