Acetic Acid → 3-Isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

HRID 604815Notes

Reaction equation

HRID 604815 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[C:12](F)([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])[NH2:8])[CH:2]([CH3:4])[CH3:3].[BH4-].[Na+].C(O)(=O)C>CS(C)=O.C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[CH:12]([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:20])[F:19])[NH2:8])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 866190023-Isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline

Product 1

HCID 866190043-Isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]anilineYield 99%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

3-Isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (874 mg, 3 mmol) was dissolved in dimethylsulfoxide (20 ml), followed by portion-wise adding sodium borohydride (340 g, 9 mmol) and stirring at 60° C. for 3 hours. The reaction solution was added with small amount of ice sequentially, followed by dropwise addition of acetic acid. The reaction solution was diluted with ethyl acetate, and washed four times with water. The solution was dried over magnesium sulfate and concentrated under reduced pressure to obtain 830 mg of the desired compound.

Workup

  1. additionThe reaction solution was added with small amount of ice sequentially
  2. washwashed four times with water
  3. dry with materialThe solution was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a26b9f025e3a44fc9cfbc47ebc70ff90
Source dataset
uspto-grants-2011_03
Patent number
US07910735B2

Reaction notes

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