Water → 3-[4-(Trifluoromethyl)phenoxy]aniline

HRID 49434

Reaction equation

HRID 49434 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].F[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.CC(C)([O-])C.[K+].O>CS(C)=O>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([O:1][C:2]2[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=2)[NH2:5])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 115683-AminophenolHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 130418683-[4-(Trifluoromethyl)phenoxy]anilineYield 57.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 3-hydroxyaniline (6.55 g) and 4-fluorobenzotrifluoride (9.85 g) in DMSO (50 mL) was added in one portion potassium tert-butoxide (7.86 g). The resulting dark solution was heated for 4 hours at 95° C., cooled to room temperature, then poured into water (600 mL). The mixture was extracted with ether (3×125 mL). The organic phase was washed with 2N sodium hydroxide (2×75 mL) and water (100 mL), dried (MgSO4) and the solvent evaporated to give a dark oil. This oil was distilled to give the title aniline as a colorless oil (8.7 g), b.p. 110-112° C. at 0.15 mm.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with ether (3×125 mL)
  3. washThe organic phase was washed with 2N sodium hydroxide (2×75 mL) and water (100 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated
  6. customto give a dark oil
  7. distillationThis oil was distilled

Sources & evidence

ORD record
ord-042a31f12e4240e89f44237b7946cf54
Source dataset
uspto-grants-2004_03
Patent number
US06706740B2

Linked notes

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