1-Chloro-4-(chloromethyl)benzene → 2-Fluoro-4-(4-chlorophenylmethoxy)nitrobenzene

HRID 1608925Notes

Reaction equation

HRID 1608925 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 200830752-Fluoro-4-(4-chlorophenylmethoxy)nitrobenzeneYield 71%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred mixture of 7.8 grams (0.05 mole) of 3-fluoro-4-nitrophenol, 8.1 grams (0.05 mole) of 4-chlorophenylmethyl chloride and 6.9 grams (0.06 mole) of potassium carbonate in 80 mL of methyl ethyl ketone was heated at reflux for about 18 hours. After this time the reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography using silica gel. Elution was accomplished using methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 10.0 grams of 2-fluoro-4-(4-chlorophenylmethoxy)nitrobenzene, mp 86°-88° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure to a residue
  5. washElution
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbf0c2166b76437bbdaaa24232e71c7d
Source dataset
uspto-grants-1995_03
Patent number
US05399543

Reaction notes

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