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

HRID 1676352Notes

Reaction equation

HRID 1676352 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 organics 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 orange brown oil. 1H NMR (400 MHz, CDCl3): δ 6.85-6.90 (m, 2H), 6.53-6.60 (m, 2H), 5.89-6.01 (m, 1H), 5.25-5.32 (m, 1H), 5.15-5.20 (m, 1H), 3.71-3.77 (m, 2H), 3.66 (br s, 1H).

Workup

  1. customThe organics 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-7d114cd5da3e48819d008acb8c5fb401
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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