Water → HCID 67046103, compound

HRID 606272Notes

Reaction equation

HRID 606272 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 949542-Fluoro-5-nitrobenzotrifluoride

Product 1

HCID 67046103HCID 67046103, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1 g of 2-Fluoro-5-Nitro benzotrifluoride (4.78 m.moles) was dissolved in 3 ml of DMF. To this solution was added 640 mg (5 m.moles) of 2-chloro-phenol and 2.76 grams of potassium carbonate. The reaction mixture was heated for 4 hours at 100° C. The reaction was cooled to room temperature and 200 ml of water added. It was then extracted 4 times with methylene chloride. The combined organic layers were dried over anhydrous magnesium sulfate and the solvent evaporated to yield a pale yellow oil. It was purified using silica-gel column chromatography (1:3 ethyl acetate hexane) to yield 1.15 g (87.5% yield) of pure 1-Chloro-2-[4-Nitro-2-(Trifluoromethyl)phenoxy]benzene as product.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionIt was then extracted 4 times with methylene chloride
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. customthe solvent evaporated
  5. customto yield a pale yellow oil
  6. customIt was purified

Sources & evidence

ORD record
ord-0670202d306b431099c555d9028b34a9
Source dataset
uspto-grants-2011_03
Patent number
US07915293B2

Reaction notes

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