Acetic Acid → HCID 64664269, compound

1-(3-Bromo-4-fluorophenyl)ethanone (5.0 g, 23.0 mmol) was dissolved in toluene (100 mL), a 3.0 M methylmagnesium chloride-tetrahydrofuran solution (11.5 mL, 34.6 mmol) was added dropwise with stirring under ice cooling, and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. Subsequently, acetic acid (1 mL) was added with stirring under ice cooling, and the mixture was stirred with heating to reflux for 4 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added with stirring under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1, v/v) to give the title compound (2.06 g; yield, 42%) as a colorless oily substance.

1. stirringthe mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour
2. stirringwith stirring under ice cooling
3. stirringthe mixture was stirred
4. temperaturewith heating
5. temperatureto reflux for 4 hours
6. stirringwith stirring under ice cooling
7. customto separate the layers
8. customThe resulting organic layer was separated
9. washwashed with saturated sodium chloride solution
10. dry with materialdried with anhydrous sodium sulfate
11. customthe solvent was evaporated under reduced pressure
12. customThe residue was purified by silica gel column chromatography (hexane

ORD record

ord-b02586abf7b54fd09590081261c3ee94

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476253B2