Isobutyraldehyde → 4-Fluoro-N-(2-methylpropyl)aniline

HRID 1049019Notes

Reaction equation

HRID 1049019 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9](=O)[CH:10]([CH3:12])[CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 97314-FluoroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 185437114-Fluoro-N-(2-methylpropyl)anilineYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoroaniline (1 g, 9 mmol) in DCM (20 mL) at room temperature was added isobutyraldehyde (985 μL, 10.8 mmol) followed by portionwise sodium triacetoxyborohydride (2.86 g, 13.5 mmol) and the reaction was stirred at room temperature for 64 hours. The reaction was concentrated and then dissolved in DCM and MeOH, dry loaded onto silica then purified by silica gel column chromatography (0-25% DCM in cyclohexane) to give (4-fluoro-phenyl)-isobutyl-amine (817 mg, 54%). LCMS (m/z, Method A) ES+ 168 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in DCM
  3. dry with materialMeOH, dry loaded onto silica
  4. customthen purified by silica gel column chromatography (0-25% DCM in cyclohexane)

Sources & evidence

ORD record
ord-2e498f357d52451daf94313dac462f19
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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