Finkelstein Reaction

Schematic representation of the Finkelstein Reaction.
Mechanism of the Finkelstein Reaction
Mechanism of the Finkelstein Reaction
Original publication
Review
Sample reactions
intermediate structure
LiCl
RT
intermediate structure
intermediate structure
MsCl, LiBr, Et3N
CH2Cl2, THF
0 °C, 3 h, 76%
intermediate structure
intermediate structure
LiBr
Acetone
RT, 72 h, 73%
"79 % yield based on 94 % conversion."
intermediate structure
intermediate structure
NaI
Acetone
Reflux, 3 h
intermediate structure
intermediate structure
LiBr
DMF
intermediate structure
intermediate structure
NaI
MEK
Reflux, 24 h, 99%
intermediate structure
intermediate structure
NaI
Acetone
Reflux, 5 d, 83%
intermediate structure
intermediate structure
NaI
MEK
85 °C, 15 h
intermediate structure
intermediate structure
NaI
MeCN
RT, 18 h, 97%
intermediate structure
intermediate structure
LiBr
Acetone
Reflux, 6 h
intermediate structure
intermediate structure
NaI, Pyr
Acetone
Reflux, 15 h
intermediate structure
intermediate structure
MsCl, Et3N, LiBr
THF
-25 °C to RT, 5 h
intermediate structure
intermediate structure
NaI
Acetone
Reflux
intermediate structure
intermediate structure
n-Bu4N+ I-
PhH
Reflux, 2 h, 75%
intermediate structure
intermediate structure
LiBr
THF
Reflux, 36 h, 84%
intermediate structure
intermediate structure
NaI
Acetone
65 °C, 16 h, 92% (3 steps)
intermediate structure