Triphenylphosphine → HCID 68662124, compound

Temperature

40 °C

(Step 2) Triphenylphosphine (1.45 g) was suspended in acetonitrile (50 ml), bromine (0.29 ml) was added, and the suspension was stirred at 40° C. for 30 min. A solution (10 ml) of 3-chloro-5-(hydroxymethyl)-N-methylbenzamide (1.1 g) obtained in Step 1 in acetonitrile was added to the reaction mixture, and the mixture was stirred at 90° C. for 5 hr. The reaction solution was quenched with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed 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=2:3) to give 3-(bromomethyl)-5-chloro-N-methylbenzamide (0.44 g).

1. stirringthe mixture was stirred at 90° C. for 5 hr
2. customThe reaction solution was quenched with aqueous sodium hydrogen carbonate solution
3. extractionextracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. additionthe obtained residue was treated by basic silica gel chromatography (ethyl acetate:hexane=2:3)

ORD record

ord-7d2e6051c0644ee5b63b25744b20dcb3

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470859B2