Acetone → 4-(3,5-Bis-trifluoromethyl-benzyl)-2-methylaniline

HRID 1640098Notes

Reaction equation

HRID 1640098 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([CH3:16])[CH:8]=1.C([O-])(=O)C.[NH4+].CC(C)=O>[Cl-].[Cl-].[Cl-].[Ti+3].O>[F:1][C:2]([F:24])([F:25])[C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:16])[CH:8]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 517165Ammonium AcetateHCID 592295044-(3,5-Bis-trifluoromethyl-benzyl)-2-methylnitrobenzene

Product 1

HCID 120027444-(3,5-Bis-trifluoromethyl-benzyl)-2-methylanilineYield 54.5%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolvent

Procedure

A solution of 20% titanium trichloride (8.4 g) was added to a mixture of 4-(3,5-bis-trifluoromethyl-benzyl)-2-methyl-nitrobenzene (0.44 g), ammonium acetate (9.3 g), acetone (20 ml) and water (10 ml) at room temperature and stirred for 12 hours. After the reaction, the reaction solution was extracted with ethyl acetate and washed with a saturated sodium bicarbonate solution and a saturated salt solution and then dried over anhydrous magnesium sulfate. After distilling the solvent off, the resultant residue was purified by silica gel column chromatography to obtain 4-(3,5-bis-trifluoromethyl-benzyl)-2-methylaniline (0.22 g).

Workup

  1. customAfter the reaction
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washwashed with a saturated sodium bicarbonate solution
  4. dry with materiala saturated salt solution and then dried over anhydrous magnesium sulfate
  5. distillationAfter distilling the solvent off, the resultant residue
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c8e082579cd34d2f917dc15441dbe3ce
Source dataset
uspto-grants-2012_02
Patent number
US08110689B2

Reaction notes

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