Anisole → 4-Fluoro-4′-methoxy-2-methyl-1,1′-biphenyl

HRID 442269Notes

Reaction equation

HRID 442269 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([CH3:9])[CH:3]=1.[C:10]1([O:16][CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[N+]([O-])=O)CC(C)C>>[CH3:9][C:4]1[CH:3]=[C:2]([F:1])[CH:8]=[CH:7][C:5]=1[C:13]1[CH:14]=[CH:15][C:10]([O:16][CH3:17])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 7519AnisoleHCID 10985Isoamyl nitrateHCID 679824-Fluoro-2-methylaniline

Product 1

HCID 214164214-Fluoro-4′-methoxy-2-methyl-1,1′-biphenyl

Procedure

A mixture of 9.0 grams of 4-fluoro-2-methyl-aniline, 200 ml. of anisole, and 9.0 grams of iso-amyl-nitrate, is warmed on a steam bath until a vigorous reaction with evolution of gas sets in. This evolution is allowed to proceed without heating until it has subsided, and the mixture is then heated on the steam bath for an additional 3 hours. The excess anisole is removed in vacuo, and the residue is chromatographed on a silica gel column using petroleum-benzin as eluent to yield 4-(2'-methyl-4'-fluorophenyl)-anisole.

Workup

  1. temperaturewithout heating until it
  2. temperaturethe mixture is then heated on the steam bath for an additional 3 hours
  3. customThe excess anisole is removed in vacuo
  4. customthe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-440d5dc52e794d35832d809e7c678de0
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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