3-(Trifluoromethyl)phenol → Benzonitrile, 5-formyl-2-[3-(trifluoromethyl)phenoxy]-

HRID 474622Notes

Reaction equation

HRID 474622 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH:10]([C:7]1[CH:8]=[CH:9][C:2]([O:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:21])[F:22])[CH:15]=2)=[C:3]([CH:6]=1)[C:4]#[N:5])=[O:11]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 27695822-Fluoro-5-formylbenzonitrile

Product 1

HCID 86666203Benzonitrile, 5-formyl-2-[3-(trifluoromethyl)phenoxy]-Yield 41.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoro-5-formylbenzonitrile (1.0 g, 6.71 mmol), 3-(trifluoromethyl) phenol (1.087 g, 6.71 mmol), K2CO3 (2.78 g, 20.12 mmol) in DMSO (20 mL) was heated at 100° C. overnight. After cooling to room temperature, the mixture was partitioned between EA (100 mL) and water (100 mL), the aqueous layer was extracted with EA (50 mL) twice. The combine the organic layers were washed with water, brine and dried over sodium sulfate, filtered, concentrated and purified via flash chromatography to afford the title compound (820 mg, 2.79 mmol, 41.6% yield). LCMS: rt=3.33 min, [M+H+]=292

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between EA (100 mL) and water (100 mL)
  3. extractionthe aqueous layer was extracted with EA (50 mL) twice
  4. washThe combine the organic layers were washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via flash chromatography

Sources & evidence

ORD record
ord-33df72a99035420b996cc10c19113c25
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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