Allyl iodide → HCID 67264487, compound

HRID 1688025Notes

Reaction equation

HRID 1688025 reaction equation
I[CH2:2][CH:3]=[CH2:4].[CH3:5][N:6]([CH3:18])[C:7]1[CH:8]=[C:9]([F:17])[C:10]([N+:14]([O-:16])=[O:15])=[C:11]([OH:13])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOCC.O>[CH2:2]([O:13][C:11]1[CH:12]=[C:7]([N:6]([CH3:18])[CH3:5])[CH:8]=[C:9]([F:17])[C:10]=1[N+:14]([O-:16])=[O:15])[CH:3]=[CH2:4]

Participants

7

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 67264300HCID 67264300, compound

Product 1

HCID 67264487HCID 67264487, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

3-Iodo-1-Propene (0.30 mL, 3.3 mmol) was added to 5-Dimethylamino-3-fluoro-2-nitro-phenol (0.592 g, 2.96 mmol) and Potassium carbonate (1.1 g, 7.9 mmol) in Dimethyl sulfoxide (15 mL) and the reaction was stirred under an atmosphere of Nitrogen for 45 m. The mixture was diluted with ether (120 mL) and water (50 mL), the layers separated and the aq. back extracted with 25 mL ether. The combined organics were washed with water (60 mL) and brine (60 mL). After drying over sodium sulfate, the solution was conc. in vacuo and the residue chromatographed (ISCO, 52 g SiO2, 0-50% EtOAc:Hex) to afford (3-Allyloxy-5-fluoro-4-nitro-phenyl)-dimethyl-amine as a yellow solid (0.61 g, 86%). 1H-NMR (CDCl3): 6.01 (m, 2H), 5.90 (s, 1H), 5.46 (d, 1H, J=17.2 Hz), 5.32 (d, 1H, J=10.6 Hz), 4.63 (m, 2H), 3.03 (s, 6H); 19F-NMR (CDCl3): −119.

Workup

  1. customthe layers separated
  2. extractionthe aq. back extracted with 25 mL ether
  3. washThe combined organics were washed with water (60 mL) and brine (60 mL)
  4. dry with materialAfter drying over sodium sulfate
  5. customthe residue chromatographed (ISCO, 52 g SiO2, 0-50% EtOAc:Hex)

Sources & evidence

ORD record
ord-bd937d97d92142028bf837c557500e31
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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