Reaction #465986

ord-5285f2cf4db24326aae4b7fbe35a23a9

Reaction equation

Nc1cc(Oc2ccc(Cl)c(Cl)c2)nc(C(=O)O)c1Cl
4-Amino-3-chloro-6-(3,4-dichlorophenoxy)pyridine-2-carboxylic acid
F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2
1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)
F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2
F-TEDA
→
Nc1c(F)c(Oc2ccc(Cl)c(Cl)c2)nc(C(=O)O)c1Cl
4-Amino-3-chloro-5-fluoro-6-(3,4-dichlorophenoxy)pyridine-2-carboxylic Acid

Reactants

Nc1cc(Oc2ccc(Cl)c(Cl)c2)nc(C(=O)O)c1Cl
4-Amino-3-chloro-6-(3,4-dichlorophenoxy)pyridine-2-carboxylic acid
F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2
1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)
F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2
F-TEDA

Reagents

None

Solvents

CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

4-Amino-3-chloro-6-(3,4-dichlorophenoxy)pyridine-2-carboxylic acid was fluorinated with [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)] (F-TEDA) in refluxing acetonitrile; mp 156-160° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06297197B1uspto-grants-2001_10