Iodopentafluoroethane → 1-Pentafluoroethyl-2-methyl-4-nitro-benzene

HRID 1770014Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[F:12][C:13](I)([F:18])[C:14]([F:17])([F:16])[F:15]>CN(C)C=O.[Cu]>[F:12][C:13]([F:18])([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11])[C:14]([F:17])([F:16])[F:15]

Participants

Conditions

Temperature: -60 °C

Procedure

A mixture of 2.36 g of 1-iodo-2-methyl-4-nitro-benzene and 2.2 g of powdered copper (Org. Synthesis Coll., Vol. II (1948), page 445 washed with water, acetone and dried under reduced pressure) in 10 ml of dimethylformamide under nitrogen in a sealed vessel was cooled to -60° C. and 11.5 g of pentafluoroethyl iodide were added. The mixture was stirred at 160° C. at a pressure of 3.5 bars for 16 hours and then cooled in ice and returned to room temperature. The mixture was poured into ice and was extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica (eluant--pentane containing 2 to 3% of dichloromethane) to obtain 1.5 g of 1-pentafluoroethyl-2-methyl-4-nitro-benzene which was hydrogenated in the presence of palladized active carbon to obtain the desired product.

Workup

temperaturecooled in ice
customreturned to room temperature
additionThe mixture was poured into ice
extractionwas extracted with ethyl acetate
washThe organic phase was washed with water
customdried
customevaporated to dryness under reduced pressure
customThe residue was chromatographed over silica (eluant--pentane containing 2 to 3% of dichloromethane)

Sources & evidence

ORD record: ord-0d88e706671745d28d20f8a5438cfdea
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05384423

Reaction notes

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