Triethylamine → 4-[(1E)-3-Cyclohexylprop-1-en-1-yl]-2-fluoroaniline

HRID 576068Notes

Reaction equation

HRID 576068 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH2:10]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:11]=[CH2:12].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:13]1([CH2:10]/[CH:11]=[CH:12]/[C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 75027AllylcyclohexaneHCID 80271Tri-o-tolylphosphineHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 867072764-[(1E)-3-Cyclohexylprop-1-en-1-yl]-2-fluoroanilineYield 69%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Toluene (5 mL) was added to 4-bromo-2-fluoroaniline (950 mg, 5.00 mmol), allylcyclohexane (1.15 mL, 7.50 mmol), palladium acetate (112 mg, 0.50 mmol), tris(2-methylphenyl)phosphine (457 mg, 1.50 mmol) and triethylamine (2.09 mL, 15.0 mmol), and the mixture was stirred, followed by heating to reflux for 10 hr. After cooling, ethyl acetate was added thereto, the mixture was filtered through Celite (registered trademark), and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a pale yellow oil (805 mg).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 10 hr
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite (registered trademark)
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

Sources & evidence

ORD record
ord-3b399ca8f6234bd1a544d2fcf1048114
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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