Borane → HCID 62049524, compound

N-(2,4-Difluorobenzyl)-4-ethylbenzamide (6.20 g, 22.5 mmol) was dissolved in freshly distilled THF (220 mL) and cooled in an ice bath under an argon atmosphere. Borane (28 mL of a 2 M solution of the dimethylsulfide complex in diethyl ether) was added and the ice bath was removed after 15 minutes. The reaction mixture was refluxed overnight and was then allowed to cool to room temperature. The reaction was quenched at 0° C. by careful addition of 10% HCl (11 mL) and the mixture was stirred at room temperature for three hours and then concentrated in vacuo. The residue was taken up in ethyl acetate (200 mL) and aqueous 2 M K2CO3 (200 mL) and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×200 mL) and the combined organic phase was washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 5.56 g (94%) of a yellow oil.

1. temperaturecooled in an ice bath under an argon atmosphere
2. customthe ice bath was removed after 15 minutes
3. temperatureThe reaction mixture was refluxed overnight
4. customThe reaction was quenched at 0° C. by careful addition of 10% HCl (11 mL)
5. concentrationconcentrated in vacuo
6. customaqueous 2 M K2CO3 (200 mL) and the phases were separated
7. extractionThe aqueous phase was extracted with ethyl acetate (2×200 mL)
8. washthe combined organic phase was washed with brine (100 mL)
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo

ORD record

ord-28c14549b8854b94a73d466b8c40da71

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07488844B2