p-Fluoronitrobenzene → 1-Ethoxy-3-(4-nitrophenoxy)benzene

HRID 1023504

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

The two reactions were performed in parallel. Two microwave vials were set up in parallel. In a large 30 mL microwave vial, 3-(ethyloxy)phenol (2 times 1.25 g, 9.045 mmol) was dissolved in 6 mL of dimethylformamide. 1-Fluoro-4-nitrobenzene (2 times 1.28 g, 9.045 mmol) and potassium carbonate (2 times 3.75 g, 27.15 mmol) were added. The reaction mixture was heated under microwave irradiation during 1 hour at 120° C. The combined reaction mixtures were filtered. The filtrated solid was washed with dichloromethane. The volatiles were evaporated under vacuum. Some dichloromethane and brine were added to this crude. The compound was extracted with dichloromethane (2 times) and ethyl acetate (2 times). The combined organic phases were dried over sodium sulphate. This afforded the title compound (4 g).

Workup

customThe combined reaction mixtures
filtrationwere filtered
washThe filtrated solid was washed with dichloromethane
customThe volatiles were evaporated under vacuum
additionSome dichloromethane and brine were added to this crude
extractionThe compound was extracted with dichloromethane (2 times) and ethyl acetate (2 times)
dry with materialThe combined organic phases were dried over sodium sulphate

Sources & evidence

ORD record: ord-740ee47c7c224185a26e3c36a5cb93bd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722695B2

Linked notes

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