Tetrahydrofuran → 4-Chloro-2-(4-fluorobenzoyl)aniline

To a 0° C. solution of 1.0M 4-fluorophenylmagnesium bromide in THF (196.6 mL, 196.6 mmol) was added a THF solution (100 mL) of 2-amino-5-chlorobenzonitrile (10.0 gm, 65.5 mmol) over 0.5 h. The ice bath was removed and the reaction stirred at ambient temperature for 17 h. The brown solution was cooled in an ice bath, treated with a drop wise addition of aqueous 1N HCl (300 mL) and extracted with ether (2×250 mL). The combined organic extracts were washed with aqueous 1N HCl (100 mL), water (2×150 ml), saturated aqueous sodium bicarbonate (150 ml), brine (100 mL), dried over MgSO4, filtered, concentrated in vacuo to 30 mL and diluted with 60 mL hexane. The resulting precipitate was filtered to give (2-amino-5-chlorophenyl)(4-fluorophenyl)methanone as a yellow solid.

1. customThe ice bath was removed
2. temperatureThe brown solution was cooled in an ice bath
3. additiontreated with a drop wise addition of aqueous 1N HCl (300 mL)
4. extractionextracted with ether (2×250 mL)
5. washThe combined organic extracts were washed with aqueous 1N HCl (100 mL), water (2×150 ml), saturated aqueous sodium bicarbonate (150 ml), brine (100 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo to 30 mL
9. additiondiluted with 60 mL hexane
10. filtrationThe resulting precipitate was filtered

ORD-Eintrag

ord-3eb8ea8114b545389be5ea5a15ffeb50

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745452B2