Potassium Iodide → HCID 66478761, compound

HRID 1746396Notes

Reaction equation

HRID 1746396 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3]O.[CH3:6][C:7]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:8]=1[NH2:9].[I-].[K+].ClCCl>O>[CH3:6][C:7]1[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][C:8]=1[NH:9][CH2:1][CH:2]([CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6344DichloromethaneHCID 6560IsobutanolHCID 27359332-Methyl-5-(trifluoromethyl)aniline

Product 1

HCID 66478761HCID 66478761, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-methyl-1-propanol (0.556 mL, 6.00 mmol), 2-methyl-5-(trifluoromethyl)aniline (525 mg, 3 mmol), potassium iodide (996 mg, 6.00 mmol) and [Cp*IrCl2]2 (33.1 mg, 0.030 mmol) were dissolved in water (2 mL). The resulting mixture was irradiated under microwaves (CEM microwave) at 170° C. for 1 hour. To the reaction mixture was added dichloromethane (5 mL) and the crude material was purified by mass directed autoprep (250 mg scale ×3, Method C, formic acid modifier). Relevant fractions were combined and evaporated to give 2-methyl-N-(2-methylpropyl)-5-(trifluoromethyl)aniline (260 mg, 1.102 mmol, 36.7% yield) as a dark yellow oil.

Workup

  1. customThe resulting mixture was irradiated under microwaves (CEM microwave) at 170° C. for 1 hour
  2. customthe crude material was purified by mass
  3. customevaporated

Sources & evidence

ORD record
ord-6e8588af082d49f98a1755fb7bd74346
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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