Reaktion #48732

Reaktionsgleichung

butylzinc bromide

3-bromo-5-fluorobenzaldehyde

→

title compound

Ausbeute 77.4%

3-butyl-5-fluorobenzaldehyde

Ausbeute 77.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeflushed with nitrogen for 18 hours
2. 2
   SonstigeSeparate the layers
3. 3
   Extraktionextract the aqueous layer with ethyl acetate (1×300 mL)
4. 4
   WaschenWash
5. 5
   Trocknendry over magnesium sulfate
6. 6
   Einengenconcentrate under reduced pressure
7. 7
   WaschenSubject residue to silica gel chromatography, eluting with 0-10% ethyl acetate in hexanes

Vorschrift

Add butylzinc bromide (49.3 mL, 24.6 mmol, 0.5 M in THF) followed by Pd(dppf)2Cl2 dichloromethane complex (1.01 g, 1.23 mmol) to a solution of 3-bromo-5-fluorobenzaldehyde (5.00 g, 24.6 mmol) in tetrahydrofuran (123.1 mL). Stir at room temperature in a sealed vessel flushed with nitrogen for 18 hours. Add saturated aqueous ammonium chloride (125 mL). Separate the layers and extract the aqueous layer with ethyl acetate (1×300 mL). Wash combined organic layers with saturated aqueous sodium chloride, dry over magnesium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with 0-10% ethyl acetate in hexanes to provide the title compound (3.43 g, 77.3%).

Quelle