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

HRID 2388625Notes

Reaction equation

HRID 2388625 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-4d4fe8bd79a3483aaaf4fef8df5de9a2
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

Loading…