Hydrochloric Acid → HCID 22349457, compound

HRID 896020Notes

Reaction equation

HRID 896020 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.CC(C)([O-])C.[K+].Cl>O.CN(C)C=O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 90154-MethoxyphenolHCID 949565-Fluoro-2-nitrotolueneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22349457HCID 22349457, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-fluoro-2-nitrotoluene (7.0 grams, 45 mmol), 4-methoxyphenol (6.2 grams, 50 mmol) and dimethylformamide (45 mL) was added potassium tert-butoxide (5.1 grams, 45 mmol). After stirring at room temperature for 24 hours, the mixture was diluted with water, acidified with 1 M aqueous hydrochloric acid, and the aqueous phase was extracted 3 times with ether. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography eluting with 0-20% ethyl acetate-hexane afforded 3.5 grams of 4-(4-methoxy-phenoxy)-2-methylnitrobenzene as a yellow solid.

Workup

  1. extractionthe aqueous phase was extracted 3 times with ether
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography
  6. washeluting with 0-20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-fd32e3c7823c47c493a1d91f31c7e917
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

Loading…