Ethanol → 4-(Trifluoromethyl)aniline

HRID 2351115Notes

Reaction equation

HRID 2351115 reaction equation
O[C:2]1([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:6][C:5](=O)[CH:4]=[CH:3]1.Cl.[NH2:14]CC(OCC)=O.C(=O)(O)[O-].[Na+].C(O)C>O>[F:10][C:9]([F:12])([F:11])[C:2]1[CH:7]=[CH:6][C:5]([NH2:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 138691094-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one

Product 1

HCID 99644-(Trifluoromethyl)anilineYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 200 mg (11 mmol) of 4-hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one, 461 mg (3.3 mmol) of ethyl glycinate hydrochloride, 336 mg (4.0 mmol) of sodium bicarbonate, and 3 mL of 95% ethanol was heated to reflux for 3 hours, allowed to cool to room temperature, and poured into 20 mL of water. The resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded a residue which was subjected to PTLC (one 2 mm silica gel plate eluted with dichloromethane) to give 102 mg (56% yield) of 4-trifluoromethylaniline.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. extractionThe resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane
  4. dry with materialCombination, drying (MgSO4), and concentration of the organic layers
  5. customafforded a residue which
  6. washwas subjected to PTLC (one 2 mm silica gel plate eluted with dichloromethane)

Sources & evidence

ORD record
ord-8d979d110beb4b38a538ea9cd0604cb3
Source dataset
uspto-grants-1989_10
Patent number
US04871877

Reaction notes

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