Ammonia → 1-Methoxy-4-(pentafluoroethyl)benzene

HRID 1844610Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2.00 g 4-iodo-anisol, 2.00 g pentafluoroethyl-trimethylsilane, 0.60 g potassium fluoride, 2.43 g copper iodide and 15 ml N,N-dimethylformamide is stirred overnight at 80° C. Then the mixture is stirred for a further 36 h at 80° C., while a further 2.00 g pentafluoroethyl-trimethylsilane are added after 4 h, 12 h and 24 h. After cooling to ambient temperature 2 M aqueous ammonia solution is added and the mixture is filtered. The filtrate is extracted with ethyl acetate, and the combined organic extracts are dried (Na2SO4) and evaporated down. The residue is chromatographed on silica gel with petroleum ether/ethyl acetate (9:1) as eluant.

Workup

additionare added after 4 h, 12 h and 24 h
additionis added
filtrationthe mixture is filtered
extractionThe filtrate is extracted with ethyl acetate
dry with materialthe combined organic extracts are dried (Na2SO4)
customevaporated down
customThe residue is chromatographed on silica gel with petroleum ether/ethyl acetate (9:1) as eluant

Sources & evidence

ORD record: ord-817f4d586cc4455a87a13460200c06fd
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946438B2

Reaction notes

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