Methanol → 4-Nitro-2-(trifluoromethyl)anisole

HRID 1603753Notes

Reaction equation

HRID 1603753 reaction equation
[Na].Cl[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[CH3:16][OH:17]>>[CH3:16][O:17][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 612132-Chloro-5-nitrobenzotrifluorideHCID 5360545Sodium

Product 1

HCID 695624-Nitro-2-(trifluoromethyl)anisoleYield 99%

Procedure

Sodium (11.78 g, 0.512 mol) was dissolved in dry methanol (1 l) and to the resulting solution was added a solution of 1-chloro-4-nitro-2-trifluoromethyl-benzene (96.22 g, 0.427 mol) in methanol (100 ml). The reaction mixture was refluxed for 3 h then cooled and evaporated in vacuo. The residue was partitioned between water (500 ml) and dichloromethane (3×400 ml). The combined organic extracts were dried (Na2SO4) and evaporated to give the title compound (93.76 g, 99%) as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. temperaturethen cooled
  3. customevaporated in vacuo
  4. customThe residue was partitioned between water (500 ml) and dichloromethane (3×400 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e0e9d21411604672a5921f33049af34a
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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