4-Fluorophenol → 1-(4-Fluorophenoxy)-3-nitrobenzene

HRID 990490Notes

Reaction equation

[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11])([O-])=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:9]2[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][CH:8]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

EX-634A) Dinitrobenzene (1.68 g, 10 mmol) and 4-fluorophenol (1.13 g, 10 mmol) were dissolved in anhydrous dimethylsulfoxide (25 mL), and powdered cesium carbonate (8 g, 24.8 mmol) was added. The mixture was stirred and heated to 100° C. using a reflux condenser under a nitrogen atmosphere. After 16 h. the mixture was diluted with water (120 mL), and the aqueous layer was extracted with diethyl ether (4×60 mL). The combined ether layers were washed with 3% HCl, 5% sodium hydroxide, and water, then dried over anhydrous MgSO4. The ether was removed in vacuo, and the recovered oil was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:25) to give 1.68 g (69%) of the desired 3-(4-fluorophenoxy)nitrobenzene product as orange crystals, 97% pure by HPLC analysis. MS m/z=234 [M+H]+.

Workup

extractionthe aqueous layer was extracted with diethyl ether (4×60 mL)
washThe combined ether layers were washed with 3% HCl, 5% sodium hydroxide, and water
dry with materialdried over anhydrous MgSO4
customThe ether was removed in vacuo
customthe recovered oil was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:25)

Sources & evidence

ORD record: ord-64438de1fa29493ea314a32e38be7462
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458849B1

Reaction notes

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