Dimethylformamide → 3-Butyl-5-fluorobenzaldehyde

Dissolve 1,3-Dibromo-5-fluoro-benzene (12.00 g, 0.05 mmol) in diethyl ether (470 mL) and cool to −78 C. Slowly add 1.6 M n-butyllithium in hexanes (29.5 mL, 49.6 mmol) and stir at −78 for one hour. Add dimethylformamide (3.45 g, 0.05 mmol) dropwise and warm to room temperature overnight. Quench with saturated aqueous ammonium chloride solution. Separate the layers and extract the organic layer (1×300 mL) with diethyl ether. Combine the organic layers and wash (1×150 mL) with water, (1×100 μL) with saturated aqueous sodium chloride and dry over magnesium sulfate. Purify using medium pressure chromatography (silica gel, 0-10% diethyl ether:hexanes) to give the desired product (4.15 g, 43%) as a yellow liquid.

1. temperaturecool to −78 C
2. customQuench with saturated aqueous ammonium chloride solution
3. customSeparate the layers
4. extractionextract the organic layer (1×300 mL) with diethyl ether
5. washwash (1×150 mL) with water, (1×100 μL) with saturated aqueous sodium chloride
6. dry with materialdry over magnesium sulfate
7. customPurify

ORD-Eintrag

ord-c476a40dfe7e47f582869f13e0b36cae

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745438B2