Water → N-Allyl-N-(4-fluorophenyl)amine

HRID 2241325Notes

Reaction equation

HRID 2241325 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH2:10][CH:11]=[CH2:12].C([O-])([O-])=O.[K+].[K+].O>C1COCC1.CCOC(C)=O>[CH2:12]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:11]=[CH2:10]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 97314-FluoroanilineHCID 11430Potassium Carbonate

Product 1

HCID 11829634N-Allyl-N-(4-fluorophenyl)amineYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-fluorobenzenamine (25 g, 225 mmol), 3-bromoprop-1-ene (19.0 ml, 225 mmol) and K2CO3 (31.1 g, 225 mmol) was stirred in THF (1 L) for 2 days. Water (20 mL) and EtOAc (1 L) were added into the reaction mixture. The organic layer was separated and washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (20% EtOAc in hexane) to afford the product (16 g, 47.0% yield) as an orange oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-a513d7b46d264a15a56d836f2288dd95
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…