Finkelstein Reaction

Schematic representation of the Finkelstein Reaction.

Mechanism of the Finkelstein Reaction

Mechanism of the Finkelstein Reaction

Original publication	Ber. Dtsch. Chem. Ges.. 1910, 43, 1528. Tetrahedron. 2011, 67, 201.
Review

Sample reactions

intermediate structure

LiCl

RT

intermediate structure

intermediate structure

Et3N, MsCl, LiBr

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

3 Å MS

MeCN

RT, 18 h, 97%

intermediate structure

intermediate structure

LiBr

Acetone

Reflux, 6 h

intermediate structure

intermediate structure

Pyr, NaI

Acetone

Reflux, 15 h

intermediate structure

intermediate structure

Et3N, MsCl, 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

intermediate structure

NaI

HMPA

110 °C, 48 h

intermediate structure

intermediate structure

LiI

THF

0 °C, 30 min

intermediate structure

intermediate structure

NaI

Acetone

Reflux

"See: J. Am. Chem. Soc. 1950, 72, 4077."

intermediate structure

intermediate structure

NaI

Acetone

45 °C, 30 h, 95% (2 steps)

intermediate structure

intermediate structure

LiI, 12-Crown-4

MeCN

Reflux, 3.5 d, 87%

intermediate structure

intermediate structure

NaI

MEK

80 °C, 40 min, 99%

intermediate structure

intermediate structure

LiBr

THF

-20 °C, 2 h, 96% (2 steps)

intermediate structure