Triphenylphosphine → 3-(Bromomethyl)-5-fluorobenzonitrile

(Step 3) Triphenylphosphine (1.91 g) was suspended in acetonitrile (50 ml), bromine (0.38 ml) was added, and the suspension was stirred for 30 min. 3-Fluoro-5-(hydroxymethyl)benzonitrile (1.1 g) synthesized by the method of Steps 1 and 2 was added to the reaction mixture, and the mixture was stirred at 85° C. for 2 hr. The reaction solution was quenched with water and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by basic silica gel chromatography (ethyl acetate:hexane=1:5) to give 3-(bromomethyl)-5-fluorobenzonitrile (0.69 g).

1. additionwas added to the reaction mixture
2. stirringthe mixture was stirred at 85° C. for 2 hr
3. customThe reaction solution was quenched with water
4. extractionextracted with ethyl acetate
5. washThe extract was washed with aqueous sodium hydrogen carbonate solution
6. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. additionthe obtained residue was treated by basic silica gel chromatography (ethyl acetate:hexane=1:5)

ORD record

ord-0535b44a460b489ebba03298913b2b7b

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470859B2