Finkelstein Reaction
Mechanism of the Finkelstein Reaction
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Sample reactions
LiCl
RT
Et3N, MsCl, LiBr
CH2Cl2, THF
0 °C, 3 h, 76%
LiBr
Acetone
RT, 72 h, 73%
"79 % yield based on 94 % conversion."
NaI
Acetone
Reflux, 3 h
LiBr
DMF
NaI
MEK
Reflux, 24 h, 99%
NaI
Acetone
Reflux, 5 d, 83%
NaI
MEK
85 °C, 15 h
NaI
3 Å MS
MeCN
RT, 18 h, 97%
LiBr
Acetone
Reflux, 6 h
Pyr, NaI
Acetone
Reflux, 15 h
Et3N, MsCl, LiBr
THF
-25 °C to RT, 5 h
NaI
Acetone
Reflux
n-Bu4N+ I-
PhH
Reflux, 2 h, 75%
LiBr
THF
Reflux, 36 h, 84%
NaI
Acetone
65 °C, 16 h, 92% (3 steps)
NaI
HMPA
110 °C, 48 h
LiI
THF
0 °C, 30 min
NaI
Acetone
Reflux
"See: J. Am. Chem. Soc. 1950, 72, 4077."
NaI
Acetone
45 °C, 30 h, 95% (2 steps)
LiI, 12-Crown-4
MeCN
Reflux, 3.5 d, 87%
NaI
MEK
80 °C, 40 min, 99%
LiBr
THF
-20 °C, 2 h, 96% (2 steps)