Lithium cyanide → 4-Fluoro-3-iodobenzeneacetonitrile

HRID 1858129Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([I:10])[CH:4]=1.[C-:11]#[N:12].[Li+]>CN(C=O)C>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:11]#[N:12])=[CH:4][C:5]=1[I:10]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Bromomethyl-1-fluoro-2-iodo-benzene (33.8 g, 107 mMol) was added to 240 mL of a 0.5M solution of lithium cyanide in DMF. The reaction mixture was heated to 80° C. under an atmosphere of dry N2 and stirred overnight at this temperature. The mixture was then cooled to ambient temperature and partitioned between Et2O and 0.1N aqueous NaOH. The Et2O layer was then washed 4 more times with 0.1N aqueous NaOH. The Et2O layer was then dried over MgSO4, fiftered and concentrated under vacuum to give 24.7 9 of the titled compound as a red solid which was used without purification.

Workup

temperatureThe mixture was then cooled to ambient temperature
custompartitioned between Et2O and 0.1N aqueous NaOH
washThe Et2O layer was then washed 4 more times with 0.1N aqueous NaOH
dry with materialThe Et2O layer was then dried over MgSO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-22fa5b1861d54e62ae9224bdd6740f34
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150377

Reaction notes

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