Dimethylformamide → HCID 68578370, Verbindung

To a mixture of 3-bromo-2,4-difluorobenzoic acid (1.00 g, 4.22 mmol), N,N-dimethylformamide (0.2 ml) and toluene (20 ml) was added under ice-cooling oxalyl dichloride (0.434 ml). The mixture was stirred at room temperature for 1 hr, and the solvent was evaporated under reduced pressure. To a solution of the residue in tetrahydrofuran (30 ml) were added N-benzylethanolamine (702 mg) and 1N aqueous sodium hydroxide solution (10 ml), and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (1.41 g, 90.3%) as a solid.

1. additionwas added under ice-
2. customthe solvent was evaporated under reduced pressure
3. additionTo a solution of the residue in tetrahydrofuran (30 ml) were added N-benzylethanolamine (702 mg) and 1N aqueous sodium hydroxide solution (10 ml)
4. stirringthe mixture was stirred at room temperature for 0.5 hr
5. extractionThe reaction mixture was extracted with ethyl acetate
6. washThe extract was washed with water and brine
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

ORD-Eintrag

ord-fee1ab5e8c82486294b8d8d2c48a03ba

Quelldatensatz

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08247403B2