Potassium Carbonate → 4-Nitro-1-(4-trifluoromethoxyphenoxy)-2-trifluoromethylbenzene

HRID 1361463Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:24][C:21]2[CH:22]=[CH:23][C:18]([O:17][C:16]([F:15])([F:25])[F:26])=[CH:19][CH:20]=2)=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixed solution composed of 44.3 g of 1-chloro-4-nitro-2-trifluoromethylbenzene, 98 mL of N,N-dimethylacetamide, 35 g of 4-trifluoromethoxyphenol, and 20.4 g of potassium carbonate was stirred with heating at 90 to 100° C. for 3 hr. This reaction solution was concentrated under the reduced pressure. Ethyl acetate was then added to and dissolved in the residue, and the solution was washed with brine. The solution was then concentrated under the reduced pressure. n-Hexane was added to the residue, and the precipitated crystals were collected by filtration to give 66.9 g of 4-nitro-1-(4-trifluoromethoxyphenoxy)-2-trifluoromethylbenzene (yield 92.7%).

Workup

concentrationThis reaction solution was concentrated under the reduced pressure
additionEthyl acetate was then added to and
dissolutiondissolved in the residue
washthe solution was washed with brine
concentrationThe solution was then concentrated under the reduced pressure
additionn-Hexane was added to the residue
filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-a052a8c0cc6c42c88cf4a2dfe6dea96a
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880006B2

Reaction notes

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