Isopropanol → 4-[(E)-2-cyclohexylethenyl]-2-fluoroaniline

HRID 576079Notes

Reaction equation

HRID 576079 reaction equation
C(O)(C)C.C(O[K])(C)(C)C.[CH:11]1(/[CH:17]=[CH:18]/B(O)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Br[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([F:30])[CH:24]=1>ICCC.O>[CH:11]1(/[CH:17]=[CH:18]/[C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([F:30])[CH:24]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 1230504-Bromo-2-fluoroanilineHCID 6031024(2-Cyclohexylvinyl)boronic acidHCID 178418922HCID 178418922, compound

Product 1

HCID 867072824-[(E)-2-cyclohexylethenyl]-2-fluoroanilineYield 99.7%

Reagents, catalysts & solvents 2

HCID 336431-IodopropaneCatalystHCID 962WaterSolvent

Procedure

Isopropanol (60 mL) was added to PEPPSI™-IPr catalyst (161 mg, 0.24 mmol) and tert-butoxy potassium (2.65 g, 23.6 mmol) under an argon atmosphere, and the mixture was stirred at room temperature for 15 min. To the reaction mixture were added trans-(2-cyclohexylvinyl)boronic acid (2.00 g, 13.0 mmol) and 4-bromo-2-fluoroaniline (2.24 g, 11.8 mmol) successively and the mixture was stirred at room temperature for 15 hr. Water was added thereto, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to afford 4-[(E)-2-cyclohexylethenyl]-2-fluoroaniline as a reddish brown oil (2.58 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c09a1b39f8f547cabadb0c5a76a78547
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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