Hydrochloric Acid → N-(4-Ethylphenyl)-2,3,5,6-tetrafluoroaniline

HRID 603336

Reaction equation

HRID 603336 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH2:4].[CH2:12]([C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)[CH3:13].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Cl>O.C1(C)C=CC=CC=1>[F:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH:4][C:17]1[CH:18]=[CH:19][C:14]([CH2:12][CH3:13])=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 127862,3,5,6-TetrafluoroanilineHCID 153131-Bromo-4-ethylbenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 21938675N-(4-Ethylphenyl)-2,3,5,6-tetrafluoroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,3,5,6-tetrafluoroaniline (4.5 g, 27.3 mmol), 4-ethylbromobenzene (5.0 g, 27 mmol), toluene (50 ml), sodium tert-butoxide (4.67 g, 48 mmol), tri-tert-butylphosphin (217 mg, 1.07 mmol) and bis-dibenzylideneacetone-palladium(0) (260 mg, 0.45 mmol) is heated under nitrogen to 85° C. for 15.5 h. The mixture is cooled to room temperature and water (30 ml), concentrated hydrochloric acid (20 ml) and hyflo are added. After stirring for 45 minutes, the mixture is filtered and the organic phase is washed with water three times. The solvent is evaporated in vacuo and the residue is chromatographed on silica using hexane/toluene (9:1 to 3:1) affording N-(2′,3′,5′,6′-tetrafluorophenyl)-4-ethylanilin as a liquid.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationthe mixture is filtered
  3. washthe organic phase is washed with water three times
  4. customThe solvent is evaporated in vacuo
  5. customthe residue is chromatographed on silica

Sources & evidence

ORD record
ord-db7c28842a0549feb90e747c0c7962f1
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Linked notes

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