Tert-butyl(dimethyl)-{[3-nitro-5-(trifluoromethyl)benzyl]oxy}silane → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-5-(trifluoromethyl)aniline

HRID 1640157Notes

Reaction equation

HRID 1640157 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([N+:18]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[Si:5]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1)[NH2:18])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 58902383Tert-butyl(dimethyl)-{[3-nitro-5-(trifluoromethyl)benzyl]oxy}silane

Product 1

HCID 589022673-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl(dimethyl){[3-nitro-5-(trifluoromethyl)benzyl]oxy}-silane (3.70 g, 11.00 mmol) in EtOAc (100 mL) was added Pd (300 mg, 10% on carbon). The reaction mixture was allowed to stir at rt overnight under an atmosphere of hydrogen. The reaction mixture was filtered through a pad of Celite and washed with EtOAc. The solvents were evaporated to give 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-(trifluoromethyl)aniline (3.32 g, 95. LCMS: (FA) ES+ 306.2.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with EtOAc
  3. customThe solvents were evaporated

Sources & evidence

ORD record
ord-b1f06a21a26f4d52a028136c0ff76814
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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