Hydrochloric Acid → 3-Chloro-5-methoxybenzonitrile

step 1—A 100 ml round bottom flask was charged under a stream of nitrogen with 3,5-dichlorobenzonitrile (R-3a,7.0 g, 40.69 mmol) and anhydrous DMF (75 mL). To the solution was added sodium methoxide (2.26 g, 44.76 mmol) and resulting solution was stirred further at RT for 24 h. When the reaction was complete, aqueous 10% HCl added dropwise to the reaction vessel. The crude mixture was extracted with EtOAc and sequentially washed with aqueous acid, water and brine. The EtOAc extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to afford a crude solid which was recrystallized from hexane/acetone to afford 5.9 g (86%) of 5-chloro-3-methoxy-benzonitrile.

1. customresulting solution
2. extractionThe crude mixture was extracted with EtOAc
3. washsequentially washed with aqueous acid, water and brine
4. dry with materialThe EtOAc extracts were dried (Na2SO4)
5. filtrationfiltered
6. customthe solvent was removed in vacuo
7. customto afford a crude solid which
8. customwas recrystallized from hexane/acetone

ORD-Eintrag

ord-7f8e5d2ac95b4b8ba3b792073f11181f

Quelldatensatz

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07906540B2