5-Fluoro-2-iodo-3-nitrotoluene → 4-Fluoro-2-methyl-6-nitrobenzonitrile

HRID 17548

Reaction equation

[Cu](C#N)[C:2]#[N:3].[F:6][C:7]1[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[C:10](I)=[C:11]([CH3:13])[CH:12]=1>CN(C)C=O>[F:6][C:7]1[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[C:10]([C:2]#[N:3])=[C:11]([CH3:13])[CH:12]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Copper cyanide (11.9 g, 133 mmol) was added to an N,N-dimethylformamide (240 ml) solution of 5-fluoro-2-iodo-1-methyl-3-nitrobenzene (I-262) (34.0 g, crude product), followed by heating at 130° C. for 3.5 hours. After cooling, the insoluble matter was removed by filtration under suction, water was added to the filtrate, and the precipitated insoluble matter was removed by filtration through Celite under suction. The filtrate was extracted with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, then the residue was subjected to column chromatography, and eluted with a mixed solvent of n-hexane/ethyl acetate (3:1, v/v) to obtain the entitled compound (17.6 g, 81% from I-235) as a red brown solid.

Workup

temperatureAfter cooling
customthe insoluble matter was removed by filtration under suction, water
additionwas added to the filtrate
customthe precipitated insoluble matter was removed by filtration through Celite under suction
extractionThe filtrate was extracted with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated away under reduced pressure
washeluted with a mixed solvent of n-hexane/ethyl acetate (3:1
customv/v) to obtain the entitled compound (17.6 g, 81% from I-235) as a red brown solid

Sources & evidence

ORD record: ord-eab29c0e19dd4feaad09e1dc1511bf3b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

Loading…