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ChemicalBook CAS DataBase List 4-amino-2-chloro-3-fluorobenzaldehyde

4-amino-2-chloro-3-fluorobenzaldehyde synthesis

2synthesis methods
-

Yield:-

Reaction Conditions:

Stage #1: 3-chloro-2-fluoroanilinewith hydrogenchloride;copper dichloride in water;dimethyl sulfoxide at 0 - 90; for 13 h;
Stage #2: with sodium hydroxide in water;dimethyl sulfoxide; pH=8;

Steps:

9.9A

To 3-chloro-2-fluoroaniline (10.0 g, 68.7 mmol) in DMSO (500 mL) was added copper (II) chloride (18.5 g, 137.4 mmol) and conc. HCl (50 mL). The whole was heated to 90° C. for 13 h. The reaction was cooled to 0° C. and 4N NaOH was added dropwise to adjust to pH 8. The reaction was diluted with water and extracted with Et2O/EtOAc (1:1). The organic layer was washed with brine, and was dried, filtered and concentrated. The resulting residue was purified via silica gel chromatography eluding with 5-30% EtOAc/hexane to provide 4-amino-2-chloro-3-fluoro-benzaldehyde (1.00 g) as a yellow powder.

References:

US2005/197359,2005,A1 Location in patent:Page/Page column 29